Vacation rentals in Chicago, United States

Carefully selected & verified rentals in Chicago, United States
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Check-out
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Rooms and Guests2 Guests, 1 Room
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481-500 out of 922
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  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
Tones Comfort Stay Near U Of Chgo And 20Min Dtwn Chgo Chicago
Map7.3 mi from City Centre900 yd from Cottage Grove
FromUS$ 141 /nightSelect
W Loop 1Br W Gym Pool In Heart Of Greektown Chi-531
Map800 yd from City Centre800 yd from Chicago Union Station
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Spacious & Stylish Home At The Heart Of Wicker Park
Map2.9 mi from City Centre700 yd from Damen (Blue Line)
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Blueground Greektown Bbq Gym Nr Willis Tower Chi-1252
Map900 yd from City Centre700 yd from Chicago Union Station
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Midway Airport 2 Bedroom With Full Kitchen
Map8.3 mi from City Centre600 yd from Midway
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Spacious Apartment In Chicago
Map9.4 mi from City Centre1500 yd from Signature Flight Support
FromUS$ 134 /nightSelect
Blueground Greektown Bbq Gym Nr Willis Tower Chi-1253
Map900 yd from City Centre700 yd from Chicago Union Station
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3Br Luxury Modern Apartment
Map1.4 mi from City Centre1400 yd from Chicago Riverwalk
FromUS$ 1 610 /nightSelect
Cute Apartment 2 Bedrooms - 12 Min From Downtown Chicagi
Map4.8 mi from City Centre1.2 mi from Spanish Coalition For Jobs
FromUS$ 526 /nightSelect
Ace Properties
Map6.2 mi from City Centre
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2Bd River North Condo With Million Dollar Views! Condo
Map1.5 mi from City Centre200 yd from Michigan Avenue
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Welcome To West Town! 2 Bedrooms And Pet Friendly Apts
Map1.9 mi from City Centre1.0 mi from United Center
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Amazing Place To Stay Near Downtown Chicago!
Map5.4 mi from City Centre
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Relax In West Town - In-Unit Laundry And Pet Friendly! Apts
Map1.9 mi from City Centre1.0 mi from United Center
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Adults Only - Walk To The United Center! Modern Touches Surround You - Check Out The Open Staircase! Apts
Map2.1 mi from City Centre700 yd from United Center
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3 Bed 2 Bath Chicago Retreat W Balcony & Parking
Map2.4 mi from City Centre
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Pet Friendly And Room For 7! Large Common Areas To Converse And Connect Apts
Map1.6 mi from City Centre300 yd from Chicago Station (Blue Line)
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Top Floor In The Heart Of West Town! Perfect For Any Group And Pet Friendly! Apts
Map1.9 mi from City Centre1.0 mi from United Center
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Lyons' Suite
Map5.8 mi from City Centre1.2 mi from Wrigley Field
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Flexible Price Range for Vacation Homes in Chicago

From cozy retreats to luxury villas – Find the ideal stay for every budget

⬆️ The highest price
US$ 2 453
⬇️ The lowest price
US$ 29
đź’¸ Average price for
Apartments
US$ 383

Top vacation homes in Chicago

Based on guest reviews from the past 12 months

Vibrant Wrigleyville Escapes:
The Double Play - 1 Min Walk To Wrigley! Spacious 2Br - Perfect For Cubs Fans!
Charming Boutique Abodes:
Luxery Stay Chicago - Themed Units! Close To Downtown, Mccormick Place & Wintrust Arena
Cultural Hotspots in Little Italy:
2F Chicago'S Little Italy Near West Loop & Downtown
Convenient Airport Access:
Days Inn Melrose Park/O'Hare South
Homey Retreats in the City:
5430 Happy Home
Urban Living with Style:
Oakwood 200 Squared

How to get to Chicago

Explore local transportation options with ease

Airports
Chicago O'Hare International (ORD)
Midway International (MDW)
Train
Chicago Union Station
Millennium Station
LaSalle Street Station
Van Buren Street Station
Dearborn Station
Garfield Boulevard \"L\"Station
Garfield Boulevard "L"Station
Millenium Station

Vacation Rentals Insights in Chicago

This guide evaluates various vacation rentals in Chicago, reviewing 7 properties to provide crucial information for your travel planning, including pricing, local fees, and prime locations.

Typical nightly rates range from $100 to $300 USD.

Peak seasons include summer (June to August) and holidays.

Local taxes and fees can add around 17% to total booking costs.

Key attractions like Millennium Park are about 1.5 miles from downtown rentals.

Book early—3 to 6 months ahead—for the best options.

Check-in
26Jun2025Select date
Check-out
27Jun2025Select date
Rooms and Guests2 Guests, 1 Room