Vacation Rentals in Chicago

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2025-09-15
2025-09-16

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2025-09-15
2025-09-16

Maximum period that can be booked is 30 days. Please enter alternative dates.

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Purple Escape
Purple Escape

Purple Escape

1618 North Rockwell Street 1, Chicago, United States
Located only 10 minutes' walk from Western underground station, the spacious 2-bedroom Purple Escape Apartment also boasts proximity to Richard's Fabulous Finds.
Stylish 1Br In Lakeview Chicago - Brompton 1 Rep
Stylish 1Br In Lakeview Chicago - Brompton 1 Rep

Stylish 1Br In Lakeview Chicago - Brompton 1 Rep

713 West Brompton Avenue, Chicago, United States
Exceptional location
This property boasts exceptional location. It has a score 9.9 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Air conditioning
Pets allowed
1-Bedroom Chic Apartment With Laundry - Brompton 55-57 Rep offers easy access to such tourist sites as Anshe Emet Synagogue, located about 5 minutes' walk away.
6 Mi To Dtwn Pet-Friendly Chicago Condo
6 Mi To Dtwn Pet-Friendly Chicago Condo

6 Mi To Dtwn Pet-Friendly Chicago Condo

4712 S St Lawrence Ave Unit 1N, Chicago, United States
Very good location
This property boasts very good location. It has a score 7 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Wi-Fi
Video games
Pets allowed
Chicago Condo Laptop Workspace, 6 Mi To Downtown! is situated approximately a 5-minute walk from Gallery Guichard and 15 km from Midway International airport. Guests can relax and unwind during their…
9.6
Excellent
The Haven, Great Location Near Downtown, Medical District And United Center
The Haven, Great Location Near Downtown, Medical District And United Center

The Haven, Great Location Near Downtown, Medical District And United Center

Excellent
8 reviews
9.6
2534 West Harrison Street, Chicago, United States
Excellent location
This property boasts excellent location. It has a score 9.4 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Express check-in/ -out
Cots
Air conditioning
No pets allowed
Staying at the spacious Great Location! 3Br With Rooftop Patio Near Downtown, Medical District And United Center, guests can relax on a terrace 6 km from the scenic Chicago Riverwalk Walkway.
8.2
Excellent
Mccormick Place 3Br Luxury Penthouse Duplex With Personal Rooftop And Optional Parking For 8 Guests In Chicago South Loop
Mccormick Place 3Br Luxury Penthouse Duplex With Personal Rooftop And Optional Parking For 8 Guests In Chicago South Loop

Mccormick Place 3Br Luxury Penthouse Duplex With Personal Rooftop And Optional Parking For 8 Guests In Chicago South Loop

Excellent
4 reviews
8.2
2036 South Michigan Avenue 710, Chicago, United States
Excellent location
This property boasts excellent location. It has a score 9.3 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Fitness centre
Cots
Air conditioning
Pets allowed
Situated only a 5-minute walk from Motor Row District, the spacious 220 m² Mccormick Place Luxury Penthouse Duplex With Personal Rooftop With Optional Parking For 8 Guests provides guests with Wi-Fi…
9.2
Excellent
K2 Sky High Apartments With Stunning Chicago Views In West Loop
K2 Sky High Apartments With Stunning Chicago Views In West Loop

K2 Sky High Apartments With Stunning Chicago Views In West Loop

Excellent
17 reviews
9.2
365 North Halsted Street 3305, Chicago, United States
Superb location
This property boasts superb location. It has a score 8.6 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Seasonal outdoor pool
Jacuzzi
Cots
Air conditioning
No pets allowed
Penthouses Near Fulton Market-Cloud9-365 is located approximately a 5-minute stroll from Hubbard Street Murals and overlooks the city. This apartment offers a private parking lot on site and modern…
10
Excellent
The Brown House - A Luxurious Uchicago Campus Stay
The Brown House - A Luxurious Uchicago Campus Stay

The Brown House - A Luxurious Uchicago Campus Stay

Excellent
3 reviews
10
6138 South Ingleside Avenue Unit 1, Chicago, United States
Superb location
This property boasts superb location. It has a score 8.3 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Air conditioning
No pets allowed
Located at a 400-metre distance from Woodlawn Baptist Church, The Brown House - A Luxurious Uchicago Campus Stay gives quick access to various tourist spots in the vicinity.
7.6
Good
City Charm Studio Apt In Chicago - Kenwood 205
City Charm Studio Apt In Chicago - Kenwood 205

City Charm Studio Apt In Chicago - Kenwood 205

Good
5 reviews
7.6
5532 South Kenwood Avenue, Chicago, United States
Exceptional location
This property boasts exceptional location. It has a score 9.5 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Air conditioning
Pets allowed
Nestled merely 250 metres from Saint Stephen's Church, City Charm Studio Apt In Chicago - Kenwood 205 offers quick access to numerous tourist attractions nearby.
10
Excellent
The Logandale: Huge Mid-Century Home, Sleeps 15
The Logandale: Huge Mid-Century Home, Sleeps 15

The Logandale: Huge Mid-Century Home, Sleeps 15

Excellent
5 reviews
10
2920 North Gresham Avenue, Chicago, United States
Exceptional location
This property boasts exceptional location. It has a score 9.5 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Children's play area
Game room
Air conditioning
No pets allowed
The Logandale: Huge Mid-Century Home, Sleeps 15 is situated around 5 minutes on foot from Saint Wenceslaus Roman Catholic Church, featuring such comforts as Wi-Fi and parking.
9
Excellent
1Br Adorable Apt With In-Unit Laundry - Lake 206 Rep
1Br Adorable Apt With In-Unit Laundry - Lake 206 Rep

1Br Adorable Apt With In-Unit Laundry - Lake 206 Rep

Excellent
3 reviews
9
630 West Lake Street, Chicago, United States
Exceptional location
This property boasts exceptional location. It has a score 10 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Air conditioning
Pets allowed
Located around 10 minutes' walk from Merchandise Mart underground station, 1Br Adorable Apt With In-Unit Laundry - Lake 206 also boasts proximity to The Athlete.
8.8
Excellent
Mixed Rustic Vibes
Mixed Rustic Vibes

Mixed Rustic Vibes

Excellent
7 reviews
8.8
320 South Richmond Street 1, Chicago, United States
Excellent location
This property boasts excellent location. It has a score 9.1 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Air conditioning
No pets allowed
The 2-room Mixed Rustic Vibes apartment lies at a distance of 3.7 km from Credit Union 1 Arena and approximately a 10-minute walk from California tube station.
8
Good
Mccormick Place Amazing 2Br Suite With City View And Optional Parking For Up To 8 Guests Near Soldier Field And Lakefront Trail
Mccormick Place Amazing 2Br Suite With City View And Optional Parking For Up To 8 Guests Near Soldier Field And Lakefront Trail

Mccormick Place Amazing 2Br Suite With City View And Optional Parking For Up To 8 Guests Near Soldier Field And Lakefront Trail

Good
4 reviews
8
2036 South Michigan Avenue Apt 304, Chicago, United States
Pleasant location
This property boasts pleasant location. It has a score 6.8 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
24-hour reception
Express check-in/ -out
Fitness centre
Cots
Air conditioning
Mccormick Place Amazing 2B-2B With City View And Optional Parking For Up To 6 Guests is located approximately 10 minutes by car from Buckingham Fountain and approximately 10 minutes by car from Grant…
9.2
Excellent
Great Chicago Getaway 2 Bedrooms Sleeps 1 To 4
Great Chicago Getaway 2 Bedrooms Sleeps 1 To 4

Great Chicago Getaway 2 Bedrooms Sleeps 1 To 4

Excellent
13 reviews
9.2
3044 West Addison Street, Chicago, United States
Superb location
This property boasts superb location. It has a score 8.6 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Air conditioning
No pets allowed
Located 10 minutes by car from Briar Street Theatre, the 1-room Great Chicago Getaway, 2 Bedrooms. Sleeps 4 To 6 features a car park for those who travel by car. About a 25-minute stroll from the…
10
Excellent
Well-Appointed Cozy Portage Park Apt, Dogs, Kids, Free Parking, 420 Compliant
Well-Appointed Cozy Portage Park Apt, Dogs, Kids, Free Parking, 420 Compliant

Well-Appointed Cozy Portage Park Apt, Dogs, Kids, Free Parking, 420 Compliant

Excellent
10 reviews
10
4134 North Mason Avenue Floor 2, Chicago, United States
Exceptional location
This property boasts exceptional location. It has a score 9.9 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Express check-in/ -out
Hiking
Non-smoking rooms
Cots
Playpen
Children's play area
Air conditioning
The spacious 1-bedroom Well-Appointed Cozy Portage Park Apt, Dogs, Kids, Free Parking, 420 Compliant Apartment is located 3.5 km from The Brickyard and offers Wi-Fi for either business or leisure.
8.8
Excellent
Luxurious Gold Coast 4Br 4-Story Villa With Parking Sleeps 12 Guests
Luxurious Gold Coast 4Br 4-Story Villa With Parking Sleeps 12 Guests

Luxurious Gold Coast 4Br 4-Story Villa With Parking Sleeps 12 Guests

Excellent
5 reviews
8.8
111 West Elm Street, Chicago, United States
Exceptional location
This property boasts exceptional location. It has a score 10 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Air conditioning
Pets allowed
The 4-bedroom Luxurious Gold Coast Villa With Parking For Up To 12 Guests offers proximity to such city sites as Ruth Page Center for the Arts Dance School, located merely a 5-minute walk away.
9.8
Excellent
Avenir West Loop Penthouses With Iconic City Views
Avenir West Loop Penthouses With Iconic City Views

Avenir West Loop Penthouses With Iconic City Views

Excellent
6 reviews
9.8
730 North Milwaukee Avenue, Chicago, United States
Excellent location
This property boasts excellent location. It has a score 9 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Cots
Air conditioning
No pets allowed
Presidential Penthouses W The Best View- Cloud9 - 730 lies about a 25-minute stroll from Ford Center Theater and about 15 minutes on foot from Grand tube station. The apartment offers a private…
10
Excellent
Bootlegger House Sleeps 10-20 Free Tv & Parking
Bootlegger House Sleeps 10-20 Free Tv & Parking

Bootlegger House Sleeps 10-20 Free Tv & Parking

Excellent
3 reviews
10
3153 North Pine Grove Avenue, Chicago, United States
Exceptional location
This property boasts exceptional location. It has a score 10 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Beach access
Tennis court
Golf course
Fishing
Cots
Baby pushchair
Game room
Air conditioning
Pets allowed
The spacious 2-bedroom Bootlegger House Sleeps 10-20 Free Tv & Parking Apartment is located approximately a 10-minute drive from Aragon Entertainment Center and offers Wi-Fi for either business or…
7.2
Good
A Home Away From Home!
A Home Away From Home!

A Home Away From Home!

Good
7 reviews
7.2
8858 South Constance Avenue, Chicago, United States
Superb location
This property boasts superb location. It has a score 8.3 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Air conditioning
No pets allowed
Offering a location around 10 minutes' drive from Tuley Park, the 3-bedroom A Home Away From Home! gives access to various tourist spots in the area.
A Terrific House For A Large Group.
A Terrific House For A Large Group.

A Terrific House For A Large Group.

4511 North Melvina Avenue, Chicago, United States
Excellent location
This property boasts excellent location. It has a score 9.4 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
The 2-bedroom A Terrific House For A Large Group. Villa is situated within 300 metres of Montrose Baptist Church, featuring such comforts as Wi-Fi and parking.
Chic Chicago Apartment About 1 Mi To Wrigley Field!
Chic Chicago Apartment About 1 Mi To Wrigley Field!

Chic Chicago Apartment About 1 Mi To Wrigley Field!

852 W Belle Plaine Ave, Chicago, United States
Exceptional location
This property boasts exceptional location. It has a score 10 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Wi-Fi
Cots
No pets allowed
Chic Chicago Apartment About 1 Mi To Wrigley Field! is located just 1.5 km from the baseball stadium "Wrigley Field" and approximately 6 km from Chicago History Museum.

All hotels in Chicago are booked for your dates. Try other dates

2025-09-15
2025-09-16

Maximum period that can be booked is 30 days. Please enter alternative dates.

Ages of children:
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Specify the age of children
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