Vacation rentals in Chicago, United States - page 5

Carefully selected & verified rentals in Chicago, United States
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Rooms and Guests2 Guests, 1 Room
Chicago boasts attractions like Millennium Park, Navy Pier, and the Art Institute of Chicago. You can also catch a game at Wrigley Field or enjoy the waterfront at Oak Street Beach. Many options await you, from boutique hotels in the West Loop to hotels with pools and pet-friendly hotels scattered throughout the city. This selection includes the best Marriott Hotels, Wyndham Hotels, and IHG Hotels for fantastic stays. Book early, especially during festivals, and use the Blue Line train to navigate easily.
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81-100 out of 719
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7.4
Very good
Perfect Wrigleyville Stay Chicago
7 adults
2 bedrooms
4 beds
Map4.8 mi from City Centre700 yd from Wrigley Field
FromUS$ 600 /nightSelect
Wonderful Home Close To Downtown Chicago - Free Parking
Map5.2 mi from City Centre
FromUS$ 149 /nightSelect
Chicago Studio Unit Cozy & Convenient - Bstone 226 Rep
Map6.2 mi from City Centre400 yd from Hyde Park
FromUS$ 235 /nightSelect
Modern And Minimalist Studio Apartment - Bstone 105 And 108 Rep
Map6.2 mi from City Centre400 yd from Hyde Park
FromUS$ 290 /nightSelect
City Charm Studio Apt In Chicago - Kenwood 205
Map6.1 mi from City Centre300 yd from MC Cormick Seminary
FromUS$ 170 /nightSelect
Chic & Fully Furnished 2Br Apartment - Roscoe 1
Map6.4 mi from City Centre800 yd from Addison Station (Blue Line)
FromUS$ 147 /nightSelect
Stylish & Bright Gem Overlooks Lovely Park With Great Amenities
Map5.8 mi from City Centre700 yd from Animal Kingdom Inc
FromUS$ 201 /nightSelect
Chic South Loop 2Br Apartment With Gym And Optional Parking Near Grant Park, Mccormick Place, Museum Campus & Downtown
Map1.7 mi from City Centre800 yd from McCormick Place
FromUS$ 252 /nightSelect
Indulging 2Br Apartment In Festive Boystown - Buckingham 1
4 adults
2 bedrooms
1 bed
Map4.6 mi from City Centre1100 yd from Wrigley Field
FromUS$ 170 /nightSelect
Iklektik House // Bluejay
Map2.7 mi from City Centre1.0 mi from United Center
FromUS$ 207 /nightSelect
1Br Adorable Apt With In-Unit Laundry - Lake 206 Rep
Map1300 yd from City Centre1000 yd from Chicago Union Station
FromUS$ 579 /nightSelect
South Loop 3Br Group Comfort Near Downtown, Grant Park, Soldier Field And Mccormick Place
Map1.7 mi from City Centre800 yd from McCormick Place
FromUS$ 278 /nightSelect
Bootlegger House Sleeps 10-20 Free Tv & Parking
Map4.4 mi from City Centre1700 yd from Wrigley Field
FromUS$ 2 310 /nightSelect
Perfect Stay - Modern 2Br Unit - Barry Gb
Map4.3 mi from City Centre1300 yd from Wrigley Field
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Vibrant 1Br Apartment In Roscoe Village - Marshfield N3
2 adults
1 bedroom
1 bed
Map5.0 mi from City Centre1500 yd from Wrigley Field
FromUS$ 266 /nightSelect
8.6
Great
5430 Happy Home
The largest option:
2 adults
1 bedroom
1 bed
Map5.6 mi from City Centre400 yd from Garfield Station (Red Line)
FromUS$ 36 /nightSelect
6.4
Nice
2F Chicago'S Little Italy Near West Loop & Downtown
Map1.3 mi from City Centre1500 yd from United Center
FromUS$ 215 /nightSelect
8.0
Great
Hollywood Rentals Llc
Map7.7 mi from City Centre1.2 mi from Loyola University Chicago
FromUS$ 9 /nightSelect
La Villita - Gateway To Chicago
Map3.9 mi from City Centre900 yd from Kedzie (Pink Line)
FromUS$ 215 /nightSelect
7.2
Very good
Luxery Stay Chicago - Themed Units! Close To Downtown, Mccormick Place & Wintrust Arena
Map1.7 mi from City Centre600 yd from McCormick Place
FromUS$ 238 /nightSelect

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Check-in
30Apr2026Select date
Check-out
01May2026Select date
Rooms and Guests2 Guests, 1 Room