Home Vacation Rentals By Owner In Chicago, IL

Showing 2040 Of 2640 Vacation Rentals
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Exceptional(8)

$493.08

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2 Charming Units in Trendy River North! Short Drive to Chicago O’Hare Airport!

Chicago, Illinois, United States

The eco-friendly boutique hotel features a prime location in River NorthbrbrThis listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 183 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 03:00 pm.brbr✦ Fitness center is available.brbr✦ Paid valet parking – 1 space(s), available for $74 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $200 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $26.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. USD 100 per pet, per staybrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Please note that the Urban Fee (Resort Fee) will be collected at the hotel.
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Exceptional(1)

$739.62

/ Nightly
Hotel

Your Home Away from Home! 3 Convenient Units, Pets Allowed! Minutes to Navy Pier

Chicago, Illinois, United States

The eco-friendly boutique hotel features a prime location in River NorthbrbrThis listing is for 3 separate rooms within a hotel. The price shown in the listing covers all 3 rooms.brbr✦ Each room is 183 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 03:00 pm.brbr✦ Fitness center is available.brbr✦ Paid valet parking – 1 space(s), available for $74 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $300 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $26.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. USD 100 per pet, per staybrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Please note that the Urban Fee (Resort Fee) will be collected at the hotel.
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Sleep 6

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Exceptional(6)

$250.09

/ Nightly
Hotel

River North Gem! Near Magnificent Mile and Chicago Riverwalk! Pets Allowed.

Chicago, Illinois, United States

The eco-friendly boutique hotel features a prime location in River NorthbrbrThis listing is for a room within a hotel.brbr✦ Your room is 183 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 03:00 pm.brbr✦ Fitness center is available.brbr✦ Paid valet parking – 1 space(s), available for $74 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $26.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. USD 100 per pet, per staybrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Please note that the Urban Fee (Resort Fee) will be collected at the hotel.
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Exceptional(23)

$479.7

/ Nightly
Apartment

Downtown Guild #3 Mag Mile Gold Coast The Lake!

Chicago, Illinois, United States

Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago!brbrGuests love our home because:br- You`re SECONDS from the LAKE and MAGNIFICENT MILEbr- Steps away from the John Hancockbr- Gym in the Basementbr- Amazing location w/ many shops & restaurants nearbybr- Fast WIFIbr- KING bedbr- Charming, vintage Chicago buildingbrbrWalk to nearly any attraction in central Chicago. Please read our FAQs to answer any questions before booking.brbr , :brbr King-Size bed with super comfy mattressbr Full bathroom with towels & body wash, shampoo, conditioner.br Full dining room with chairs & utensils/pots/pans/dinnerware/glassesbr Custom kitchen stocked w/ all SS appliancesbr Beautiful, Gilded Designer Apartmentbrbr :brLiving/dining room has 50” SMART TVbrCLOSE TO LAKE, SHOPPING, AND RESTAURANTS.brbrPlease note that we have a single duct HVAC system. The building is required by law to turn on/off heat and air at specific times. With this, we understand that it can be uncomfortable in the transition dates and we work to accommodate our guests with fans or indoor heaters. brbr brbr : brA: Very much so. 24 hours a day.brbr : brA: You do not need a car, but there are multiple garages within a block of the home if you drive. They are typically $20-40 / night. We recommend apps like SpotAngels or SpotHero to find free or cheap parking. There are SpotHero spots near the building for your convenience, available on a first come, first serve basis.brbr : , , brA: Nope! we provide all these things. We also provide you with a starter pack of toilet papers.brbr : brA: Check in is 4pm and check out is 10am. Early check ins can be difficult if there are guests who checked out same day. We ask for an early check-in, or a late-check out fee, if you request either.brbr : brA: Yes. And we wouldn`t trust any listing with which this isn`t the case.brbr : brA: Yes, and we take pride in providing a clean home for guests.brbr : ` brA: We honestly have no idea. With fees included, it only shows the guest how much they pay. This figure should be present after you enter your dates. Note that, pricing varies on a daily basis, and it actually uses some crazy algorithm to adjust it automatically, so I don`t actually control this.brbr : brA: Very. Some guests say they`re the best they`ve ever slept on!brbr : - / brA: If you do not have flights that coincide with our check-in and checkout times, you may use RadicalStorage or Bounce to store your bags for your optimal time :)brbrNo Agency Relationship. Nothing herein contained shall be deemed to authorize or empower either party to act as agent for the other party to this Agreement, or to conduct business in the name, or for the account, of the other party to this Agreement.brbrYou have full access to the condo and the gym. Please respect the long-term tenants in the building and do not disclose that you are staying for your safety+security.brbrWe are here as you need us, but give you space to enjoy.brbrWe are close to most everything - Lake Michigan, Michigan Ave, Navy Pier, and so much more.brbrWe recommend NOT renting a car. We are so central that you are best Uber-ing where you want to go.brbrNo Local Guests (City or Suburbs)brQuiet hours: 10pm to 8ambrMinimum age of 25 to bookbrbr Last-Minute Bookings PolicybrTo ensure a smooth check-in, all same-day reservations will REQUIRE HOST APPROVAL. Please message us first so we can confirm and ensure everything is set for your arrival. This helps us make sure the space is properly prepared and ready for your stay.brbrThe base price for this home is for 2 guests only. There will be an extra guest fee of $15 per guest per night if your group exceeds to 2 people.brbr br - $250.00 plus any damages or additional cleaning costs incurredbrbrNo Animal PolicybrPlease note that the building has strict no-animal policies in place, which include service animals and emotional support animals. These restrictions are managed by building management and apply to all residents and guests for health and safety reasons.brbr -Up to the cost of any impacted nights subsequent to originally scheduled check-outbr / - $500.00 minimum charge and eviction from Rental Unitbr - Up to $125.00 per hour of additional cleaning neededbr - Varies depending on cost of itembrbr : potential warning issued or, if necessary, eviction with no refund and a charge of up to $1,000.00br - Up to $2,000.00br - $75 minimum charge for handling and shipping.brIf keys are left inside the home, and we come to give you re-entry it is $50.br - $50.00 minimum chargebr - $150.00 minimum chargebrNo Unauthorized Late Check Out without notice from Host.br-Early check-ins/Late check-outs can sometimes be accommodated by our cleaning service for $50 per hour fee.brbrThere is a NOISE MONITORING system within the home to track decibel noise level. Please respect our neighbors and do not get too loud outside quiet hours :)brbrAll guest names and ages must be registered before you are allowed to check in.brbrGuest VerificationbrAs part of our vetting process, we may ask guests to confirm a few details — such as their names, ages, where they’re traveling from, or their travel plans — before accepting a booking. In some cases, we may also request a valid government-issued ID for verification purposes. This helps us ensure that all stays are safe, transparent, and in line with our house policies.brbrUnresponsive GuestbrIn some cases, if a guest does not respond within a reasonable period, we reserve the right to cancel the reservation. brFor same-day bookings, this timeframe is up to 2 hours or less. For all other bookings, this timeframe is up to 8 hours. This ensures that we can provide the best experience and availability for all our guests.brbrOnline Check-In & Rental Agreement RequiredbrBefore receiving check-in instructions, all primary guests must complete our online check-in form and review/sign our rental agreement. This helps verify guest details and ensures a smooth, secure arrival.brbrEXTRA GUEST CHARGEbrThe base price covers 2 guests. For more than 2 guests, there is an extra guest fee of $15 per guest for the full number of nights.brExample: 1 extra guest for a 5-night stay = $15 × 5 nights = $75.brbrRefundable Security Deposit: A $300 refundable security deposit is required and will be `held` or `authorized` (not `charged`) by Chicago Hospitality Club on your card. Any property damage or extra charges may be deducted from the deposit. VRBO collects platform payments/charges separately, while Chicago Hospitality Club handles the deposit, so seeing both on your statement is normal. The deposit is automatically released 3-7 days after checkout.brbrKeys & AirTags:brFor transparency, some building keys or fobs may have an AirTag attached for loss prevention. The AirTag is only used to locate the key if it is lost and is never used to track guests or their movements. Guests are not required to carry the key at all times, but we recommend keeping the AirTag attached to help avoid replacement charges if the key is misplaced.brbrSecurity Deposit (Families with Young Children)brA security deposit may be required for groups traveling with two or more children under 14 years old, as a precaution against accidental damage. The deposit is fully refundable, provided there is no damage to the property after a standard post-checkout inspection.brbrRefund Processing PolicybrIn the event of a guest-initiated cancellation, any bank fees or payment processing charges incurred will be the responsibility of the guest and will be deducted from the refund amount.brbrNo Local Guests (City or Suburbs)brQuiet hours: 10pm to 8ambrMinimum age of 25 to bookbrbrLast-Minute Bookings PolicybrTo ensure a smooth check-in, all same-day reservations will REQUIRE HOST APPROVAL. Please message us first so we can confirm and ensure everything is set for your arrival. This helps us make sure the space is properly prepared and ready for your stay.brbr -Up to the cost of any impacted nights subsequent to originally scheduled check-outbr / - $500.00 minimum charge and eviction from Rental Unitbr - Up to $125.00 per hour of additional cleaning neededbr - Varies depending on cost of item
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$135.97

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Landing | Incredible 1BD, Yoga Studio, Pool

Chicago, Illinois, United States

Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full kitchens, in-unit laundry, fast WiFi, stylish furnishings, and a dedicated workspace. Stay productive with a coworking lounge and private workstations, enjoy skyline views from indoor and outdoor rooftop lounges, and keep active at the fitness center with private studio. Plus, enjoy 24-hour concierge, bike storage, pet wash station, and EV charging.br Guest ScreeningbrAll guests must complete CLEAR ID verification and a background check (no evictions, collections, or criminal records).brA passport is required for international guests.brbrStays of 30+ NightsbrThe primary guest must complete a soft credit check (minimum score of 550) and provide a valid SSN.brbrAfter BookingbrWe will request your email address to send a secure check-in link.brbrCredit Card RequirementbrA valid credit card is required to complete the check-in process and secure the reservation.brbrParking InformationbrParking availability, arrangements, and fees vary by property and are managed by third-party providers in some locations. Costs may apply. Please contact us prior to booking to receive specific details for your selected property.brbrPet PolicybrPet fee: $50 per pet, per stay (for stays under 30 nights); $150 per pet, per month (for stays of 30 nights or longer).brOur member service team will promptly reach out and share all details prior to your arrival.
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Sleep 2

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$155.86

/ Nightly
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Landing | Chic 1BD, Pool, Yoga Studio

Chicago, Illinois, United States

Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full kitchens, in-unit laundry, fast WiFi, stylish furnishings, and a dedicated workspace. Stay productive with a coworking lounge and private workstations, enjoy skyline views from indoor and outdoor rooftop lounges, and keep active at the fitness center with private studio. Plus, enjoy 24-hour concierge, bike storage, pet wash station, and EV charging.br Guest ScreeningbrAll guests must complete CLEAR ID verification and a background check (no evictions, collections, or criminal records).brA passport is required for international guests.brbrStays of 30+ NightsbrThe primary guest must complete a soft credit check (minimum score of 550) and provide a valid SSN.brbrAfter BookingbrWe will request your email address to send a secure check-in link.brbrCredit Card RequirementbrA valid credit card is required to complete the check-in process and secure the reservation.brbrParking InformationbrParking availability, arrangements, and fees vary by property and are managed by third-party providers in some locations. Costs may apply. Please contact us prior to booking to receive specific details for your selected property.brbrPet PolicybrPet fee: $50 per pet, per stay (for stays under 30 nights); $150 per pet, per month (for stays of 30 nights or longer).brOur member service team will promptly reach out and share all details prior to your arrival.
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$141.8

/ Nightly
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Landing | Stunning 1BD, Rooftop Lounge, Pool

Chicago, Illinois, United States

Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full kitchens, in-unit laundry, fast WiFi, stylish furnishings, and a dedicated workspace. Stay productive with a coworking lounge and private workstations, enjoy skyline views from indoor and outdoor rooftop lounges, and keep active at the fitness center with private studio. Plus, enjoy 24-hour concierge, bike storage, pet wash station, and EV charging.br Guest ScreeningbrAll guests must complete CLEAR ID verification and a background check (no evictions, collections, or criminal records).brA passport is required for international guests.brbrStays of 30+ NightsbrThe primary guest must complete a soft credit check (minimum score of 550) and provide a valid SSN.brbrAfter BookingbrWe will request your email address to send a secure check-in link.brbrCredit Card RequirementbrA valid credit card is required to complete the check-in process and secure the reservation.brbrParking InformationbrParking availability, arrangements, and fees vary by property and are managed by third-party providers in some locations. Costs may apply. Please contact us prior to booking to receive specific details for your selected property.brbrPet PolicybrPet fee: $50 per pet, per stay (for stays under 30 nights); $150 per pet, per month (for stays of 30 nights or longer).brOur member service team will promptly reach out and share all details prior to your arrival.
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Sleep 2

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$139.53

/ Nightly
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Landing | Spectacular 1BD, Rooftop Lounge, Gym

Chicago, Illinois, United States

Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full kitchens, in-unit laundry, fast WiFi, stylish furnishings, and a dedicated workspace. Stay productive with a coworking lounge and private workstations, enjoy skyline views from indoor and outdoor rooftop lounges, and keep active at the fitness center with private studio. Plus, enjoy 24-hour concierge, bike storage, pet wash station, and EV charging.br Guest ScreeningbrAll guests must complete CLEAR ID verification and a background check (no evictions, collections, or criminal records).brA passport is required for international guests.brbrStays of 30+ NightsbrThe primary guest must complete a soft credit check (minimum score of 550) and provide a valid SSN.brbrAfter BookingbrWe will request your email address to send a secure check-in link.brbrCredit Card RequirementbrA valid credit card is required to complete the check-in process and secure the reservation.brbrParking InformationbrParking availability, arrangements, and fees vary by property and are managed by third-party providers in some locations. Costs may apply. Please contact us prior to booking to receive specific details for your selected property.brbrPet PolicybrPet fee: $50 per pet, per stay (for stays under 30 nights); $150 per pet, per month (for stays of 30 nights or longer).brOur member service team will promptly reach out and share all details prior to your arrival.
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$142.97

/ Nightly
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Landing | Spectacular 1BD, Yoga Studio, Pool

Chicago, Illinois, United States

Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full kitchens, in-unit laundry, fast WiFi, stylish furnishings, and a dedicated workspace. Stay productive with a coworking lounge and private workstations, enjoy skyline views from indoor and outdoor rooftop lounges, and keep active at the fitness center with private studio. Plus, enjoy 24-hour concierge, bike storage, pet wash station, and EV charging.br Guest ScreeningbrAll guests must complete CLEAR ID verification and a background check (no evictions, collections, or criminal records).brA passport is required for international guests.brbrStays of 30+ NightsbrThe primary guest must complete a soft credit check (minimum score of 550) and provide a valid SSN.brbrAfter BookingbrWe will request your email address to send a secure check-in link.brbrCredit Card RequirementbrA valid credit card is required to complete the check-in process and secure the reservation.brbrParking InformationbrParking availability, arrangements, and fees vary by property and are managed by third-party providers in some locations. Costs may apply. Please contact us prior to booking to receive specific details for your selected property.brbrPet PolicybrPet fee: $50 per pet, per stay (for stays under 30 nights); $150 per pet, per month (for stays of 30 nights or longer).brOur member service team will promptly reach out and share all details prior to your arrival.
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Sleep 2

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$137.14

/ Nightly
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Landing | Beautiful 1BD, Gym, Yoga Studio

Chicago, Illinois, United States

Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full kitchens, in-unit laundry, fast WiFi, stylish furnishings, and a dedicated workspace. Stay productive with a coworking lounge and private workstations, enjoy skyline views from indoor and outdoor rooftop lounges, and keep active at the fitness center with private studio. Plus, enjoy 24-hour concierge, bike storage, pet wash station, and EV charging.br Guest ScreeningbrAll guests must complete CLEAR ID verification and a background check (no evictions, collections, or criminal records).brA passport is required for international guests.brbrStays of 30+ NightsbrThe primary guest must complete a soft credit check (minimum score of 550) and provide a valid SSN.brbrAfter BookingbrWe will request your email address to send a secure check-in link.brbrCredit Card RequirementbrA valid credit card is required to complete the check-in process and secure the reservation.brbrParking InformationbrParking availability, arrangements, and fees vary by property and are managed by third-party providers in some locations. Costs may apply. Please contact us prior to booking to receive specific details for your selected property.brbrPet PolicybrPet fee: $50 per pet, per stay (for stays under 30 nights); $150 per pet, per month (for stays of 30 nights or longer).brOur member service team will promptly reach out and share all details prior to your arrival.
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$141.87

/ Nightly
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Landing | Spectacular 1BD, Gym, Yoga Studio

Chicago, Illinois, United States

Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full kitchens, in-unit laundry, fast WiFi, stylish furnishings, and a dedicated workspace. Stay productive with a coworking lounge and private workstations, enjoy skyline views from indoor and outdoor rooftop lounges, and keep active at the fitness center with private studio. Plus, enjoy 24-hour concierge, bike storage, pet wash station, and EV charging.br Guest ScreeningbrAll guests must complete CLEAR ID verification and a background check (no evictions, collections, or criminal records).brA passport is required for international guests.brbrStays of 30+ NightsbrThe primary guest must complete a soft credit check (minimum score of 550) and provide a valid SSN.brbrAfter BookingbrWe will request your email address to send a secure check-in link.brbrCredit Card RequirementbrA valid credit card is required to complete the check-in process and secure the reservation.brbrParking InformationbrParking availability, arrangements, and fees vary by property and are managed by third-party providers in some locations. Costs may apply. Please contact us prior to booking to receive specific details for your selected property.brbrPet PolicybrPet fee: $50 per pet, per stay (for stays under 30 nights); $150 per pet, per month (for stays of 30 nights or longer).brOur member service team will promptly reach out and share all details prior to your arrival.
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$133.71

/ Nightly
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Landing | Chic 1BD, Gym, Rooftop Lounge

Chicago, Illinois, United States

Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full kitchens, in-unit laundry, fast WiFi, stylish furnishings, and a dedicated workspace. Stay productive with a coworking lounge and private workstations, enjoy skyline views from indoor and outdoor rooftop lounges, and keep active at the fitness center with private studio. Plus, enjoy 24-hour concierge, bike storage, pet wash station, and EV charging.br Guest ScreeningbrAll guests must complete CLEAR ID verification and a background check (no evictions, collections, or criminal records).brA passport is required for international guests.brbrStays of 30+ NightsbrThe primary guest must complete a soft credit check (minimum score of 550) and provide a valid SSN.brbrAfter BookingbrWe will request your email address to send a secure check-in link.brbrCredit Card RequirementbrA valid credit card is required to complete the check-in process and secure the reservation.brbrParking InformationbrParking availability, arrangements, and fees vary by property and are managed by third-party providers in some locations. Costs may apply. Please contact us prior to booking to receive specific details for your selected property.brbrPet PolicybrPet fee: $50 per pet, per stay (for stays under 30 nights); $150 per pet, per month (for stays of 30 nights or longer).brOur member service team will promptly reach out and share all details prior to your arrival.
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$135.97

/ Nightly
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Landing | Stunning 1BD, Gym, Rooftop Lounge

Chicago, Illinois, United States

Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full kitchens, in-unit laundry, fast WiFi, stylish furnishings, and a dedicated workspace. Stay productive with a coworking lounge and private workstations, enjoy skyline views from indoor and outdoor rooftop lounges, and keep active at the fitness center with private studio. Plus, enjoy 24-hour concierge, bike storage, pet wash station, and EV charging.br Guest ScreeningbrAll guests must complete CLEAR ID verification and a background check (no evictions, collections, or criminal records).brA passport is required for international guests.brbrStays of 30+ NightsbrThe primary guest must complete a soft credit check (minimum score of 550) and provide a valid SSN.brbrAfter BookingbrWe will request your email address to send a secure check-in link.brbrCredit Card RequirementbrA valid credit card is required to complete the check-in process and secure the reservation.brbrParking InformationbrParking availability, arrangements, and fees vary by property and are managed by third-party providers in some locations. Costs may apply. Please contact us prior to booking to receive specific details for your selected property.brbrPet PolicybrPet fee: $50 per pet, per stay (for stays under 30 nights); $150 per pet, per month (for stays of 30 nights or longer).brOur member service team will promptly reach out and share all details prior to your arrival.
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Exceptional(8)

$409.02

/ Nightly
Condo

Soft Palate & Warm Bricks At A Rogers Park Home

Chicago, Illinois, United States

Meet NEW and CHARM with exposed brick, dim LED lighting,rainfall shower with bluetooth wiring, In-unit washer/dryer, open shelving, gourmet kitchen seats 6, stainless steel appliances, Custom wood counters,5 range oven w/Broan hood, soft close cabinets,coffee machine or walk to Starbucks across the street. Grocery store(Jewel), UPS,Walgreens, Marshalls, LA Fitness, wine shop, Red Line, Metra, CTA Transportation, Evanston, Lake,Beaches, and Restaurants all in walking distance.Loyola and Northwestern 10 minutes away...Only bring your clothes and your ready to go!brbrCleaning fee is $355 for stays of 30 days or less; additional Flat $150 per 30-days for longer term stays. Also, look at our other 2 units in the building.brbrHouse Rules:br-Upon booking we require a list of all full legal names of you and your guests, a four digit code to gain access to the building, a copy of the driver's license, state ID or passport (must submit to owner at the time of booking)br-No additional guests allowed if not on the list ($100 per night, per guest if not authorized). br-Additional guests: $45 per person, per diem.br-Must reserve the amount of parking spots needed. First come, first served.br-First parking spot free, (additional vehicle $25 per diem, per vehicle)br-Early Check-In Fee: $45br-No street shoes worn in building at all times ($100 fine)br-No Pets. ($500 Fine)br-No smoking allowed in building ($1,000 fine)br-Unauthorized gathering or party is fined at $500 nightly.brbrCheck out our other two units...brVRBO 1351676brVRBO 1348787
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$297.25

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Cozy 2BR, 1.5 BA Apt w/Utilities-Vibrant Area, Walk to Lake, Trains&Restaurants

Chicago, Illinois, United States

This fully remodeled 2-bedroom, 1.5-bath garden apartment offers a rare mix of privacy, space, and location in one of Chicago's most vibrant neighborhoods. Sitting half above and half below ground level in a stunning bow-front brick building, the unit features its own private entrance and a fresh, modern interior from top to bottom; everything, from the plumbing to the electrical, has been updated. It's quiet, peaceful, and full of thoughtful upgrades that make daily life more comfortable.brbrWith 1,500 square feet of living space, the apartment feels open and airy, thanks to plenty of windows that bring in natural light throughout the day. The hardwood floors in the main living areas lend the space a warm ambiance, while the bathrooms have tile floors. You'll love spending time in the bright living area, complete with a comfortable sofa and smart TV, perfect for relaxing nights in.brbrThe brand-new kitchen is fully equipped with high-quality, never-used appliances, a sleek electric stovetop, and ample cabinet storage. Plus, there's an entire wall dedicated to extra storage, perfect for organizing pantry items or kitchen tools. Whether you're a regular cook or simply prefer having a well-equipped setup when needed, this kitchen checks all the boxes.brbrThe second bedroom can be easily converted into a home office if needed. The primary bedroom features a king-sized bed with a tempered mattress that can be split into two twin beds for roommates, guests, kids, or a more customized setup. It also includes blackout shades and an extra-large double walk-in closet. The second bedroom features two full walk-in closets, providing you with more storage space than most apartments. Both bedrooms include blackout shades, making it easy to sleep in or block out afternoon light.brbrYou also have a washer and dryer in-unit, and all utilities are included, making this a highly convenient place to live. The apartment is wired with a hardwired smoke and carbon monoxide detection system, and recessed can lighting throughout adds to the modern, clean look.brbrThere's a beautiful patio just outside, currently restricted, but access can be arranged with the landlord upon request. Street parking is easy and no permit is required, and you're just half a block from several bus lines, five blocks from the Berwyn train station, and steps from Divvy bike rentals. Getting around the city from here couldn't be easier.brbrThis is hands down one of Chicago's best neighborhoods. You're just off Clark Street in the heart of the action, surrounded by dozens of excellent restaurants, unique shops, and everything you could need; grocery stores, pharmacies, and healthcare are all within walking distance. This area is buzzing with energy, but your apartment keeps you tucked into your own quiet corner.brbrNature lovers and dog walkers will appreciate being close to Foster Beach, Lake Michigan, the Montrose Bird Sanctuary, and Montrose Harbor, all of which are easily accessible within a 15-minute walk. It's a rare blend of city convenience and outdoor access that really sets this location apart.
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$324.02

/ Nightly
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Burnham Two Queen - Staypineapple's Historic Charm Next to Navy Pier

Chicago, Illinois, United States

This listing is for a room within a hotel.brbr✦ Your room is 172 sq. ft, equipped with complimentary toiletries, high definition 50-inch TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 18 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center is available, available in the property.brbr✦ Paid valet parking – 1 space(s), available for $75 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $24.95 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $29.95 (per night).brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.
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$322.85

/ Nightly
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Elegant Room w/ Modern Conveniences & Walkable to Major Attractions

Chicago, Illinois, United States

This listing is for a room within a hotel.brbr✦ Your room is 172 sq. ft, equipped with complimentary toiletries, high definition 50-inch TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 18 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center is available, available in the property.brbr✦ Paid valet parking – 1 space(s), available for $75 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $24.95 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $29.95 (per night).brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.
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$291.07

/ Nightly
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Cozy Room w/ Historic Charm & Modern Amenities in Heart of Chicago

Chicago, Illinois, United States

This listing is for a room within a hotel.brbr✦ Your room is 172 sq. ft, equipped with complimentary toiletries, high definition 50-inch TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 18 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center is available, available in the property.brbr✦ Paid valet parking – 1 space(s), available for $75 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $24.95 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $29.95 (per night).brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.
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$301.76

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Burnham King - Staypineapple Chicago Charm & Afternoon Delights in The Loop

Chicago, Illinois, United States

This listing is for a room within a hotel.brbr✦ Your room is 180 sq. ft, equipped with complimentary toiletries, high definition 50-inch TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 18 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center is available, available in the property.brbr✦ Paid valet parking – 1 space(s), available for $75 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $24.95 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $29.95 (per night).brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.
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