Vacation rentals in Chicago, United States - page 2

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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21-40 out of 719
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Foundry Unmatched Skyline Views At Lincoln Park Apartment Chicago
Map2.3 mi from City Centre500 yd from North/Clybourn
FromUS$ 813 /nightSelect
A Hidden Gem, Approx 15 Mins To Downtown Chicago! Apartment
Map6.2 mi from City Centre700 yd from Applied Research Technical
FromUS$ 88 /nightSelect
8.0
Great
Stylish 2Br Pad With Up-To-Date Comforts - Halsted Rep
4 adults
2 bedrooms
1 bed
Map4.8 mi from City Centre800 yd from Wrigley Field
FromUS$ 639 /nightSelect
The Chic Urban Oasis Near The Lake!
Map8.7 mi from City Centre500 yd from Jazz Unites Inc
FromUS$ 136 /nightSelect
The Roscoe Village Guesthouse
Map5.0 mi from City Centre700 yd from Paulina
FromUS$ 282 /nightSelect
7.0
Very good
Superior
8 adults
3 bedrooms
4 beds
Map1.8 mi from City Centre1.1 mi from United Center
FromUS$ 395 /nightSelect
Afrique Francaise De Woodlawn 1
Map7.1 mi from City Centre800 yd from King Drive
FromUS$ 32 /nightSelect
City Villa Sleeps 10-20 Free Tv & Parking
Map4.4 mi from City Centre1700 yd from Wrigley Field
FromUS$ 234 /nightSelect
Game Day Getaway - 3Br In Vibrant Wrigleyville
Map5.3 mi from City Centre700 yd from Wrigley Field
FromUS$ 252 /nightSelect
Cozy 2 Brm Apartment Mins Away From United Center
Map2.9 mi from City Centre1.1 mi from United Center
FromUS$ 181 /nightSelect
Bella Villa On Taylor Street Chicago'S Little Italy 1 Mile West The Loop & Uic
Map1.3 mi from City Centre1.0 mi from United Center
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The Twin Lions: Bespoke Travel Lodge W/ Speakeasy*
Map3.3 mi from City Centre900 yd from Damen (Blue Line)
FromUS$ 237 /nightSelect
Stylish 2Br Stunner In Unbeatable Location
Map2.8 mi from City Centre1000 yd from Damen (Blue Line)
FromUS$ 194 /nightSelect
Modern 3Br In South Loop With Optional Parking And Gym Access Near Mccormick Place, Chinatown And Soldier Field
Map1.7 mi from City Centre800 yd from McCormick Place
FromUS$ 787 /nightSelect
Mccormick Place Beautiful 2Br Apartment With Optional Parking Sleeps Up To 8 Near Soldier Field, Grant Park And Lakefront Trail
Map1.7 mi from City Centre800 yd from McCormick Place
FromUS$ 459 /nightSelect
9.8
Perfect
Webster House
3 adults
1 bedroom
2 beds
Map3.2 mi from City Centre400 yd from Lincoln Park Hospital
FromUS$ 230 /nightSelect
8.6
Great
Wrigleyville Friends Unit - 5Bdrm
7 adults
5 bedrooms
5 beds
Map4.8 mi from City Centre700 yd from Wrigley Field
FromUS$ 225 /nightSelect
Entire Modern 2 Bedroom Apartment
4 adults
2 bedrooms
3 beds
Map6.9 mi from City Centre400 yd from
FromUS$ 79 /nightSelect
The Wrigleyville Vip-200 Steps From Wrigley Field
Map5.0 mi from City Centre400 yd from Wrigley Field
FromUS$ 453 /nightSelect
The Banksy-Free Parking -4 Bedroom W King Bed- Firepit Rooftop Near United Center
Map2.3 mi from City Centre1100 yd from United Center
FromUS$ 1 282 /nightSelect

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