Vacation rentals in Chicago, United States

Carefully selected & verified rentals in Chicago, United States
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26Jun2025Select date
Check-out
27Jun2025Select date
Rooms and Guests2 Guests, 1 Room
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801-820 out of 922
Sort by: high popularity
  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
Central & Comfy 2 Bedroom I West Loop I Free Parking O Chicago
Map2.3 mi from City Centre1700 yd from United Center
FromUS$ 116 /nightSelect
Chic South Loop 2Br Apartment With Gym And Optional Parking Near Grant Park, Mccormick Place, Museum Campus & Downtown Chicago
Map1.7 mi from City Centre800 yd from McCormick Place
FromUS$ 110 /nightSelect
3Br Inviting Apartment With In-Unit Washer & Dryer - Touhy 3N
Map9.5 mi from City Centre1800 yd from Loyola University Chicago
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Urbaneden Loft Apartment
Map4.1 mi from City Centre800 yd from Hartgrove Hospital
FromUS$ 153 /nightSelect
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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Gold Coast Villa Next To Oak Street Beach
Map1.9 mi from City Centre900 yd from Michigan Avenue
FromUS$ 792 /nightSelect
1Br Vintage Apartment Close To Shops & Dining - Montrose 1B Rep
Map8.3 mi from City Centre1100 yd from Montrose Station (Blue Line)
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Cozy 3Br Modern Home With Optional Parking Near Mccormick Place, Museum Campus And Soldier Field
Map1.6 mi from City Centre1000 yd from McCormick Place
FromUS$ 199 /nightSelect
Studio Apt With Laundry, Near Shops! - Montrose 316 & 318
Map5.9 mi from City Centre1700 yd from Wrigley Field
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Prime & Stylish 1Br Hideaway - Dorchester 306
Map5.9 mi from City Centre
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Roomy 3Br Apartment Near Beach - Lunt 33-2N
Map9.3 mi from City Centre1500 yd from Loyola University Chicago
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Comfortable Minimalist Studio Apt - Dorchester 203
Map5.9 mi from City Centre
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Sleek & Spacious 3Br Apartment - Hyde Park 1004
Map5.7 mi from City Centre
FromUS$ 542 /nightSelect
Blueground Elmhurst Pool Nr Elmhurst Art Museum Chi-1264
Map15.7 mi from City Centre
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City Charm 1-Bedroom Oasis - Woodlawn 1E
Map5.9 mi from City Centre
FromUS$ 223 /nightSelect
Beautifully Remodeled Second Floor Flat In River North With Private Rooftop - 2S
Map1.5 mi from City Centre1300 yd from Michigan Avenue
FromUS$ 524 /nightSelect
Walk To Metra Long-Term Getaway In Chicago!
Map8.5 mi from City Centre
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Breathtaking Chi Unit In River North With Rooftop Deck - Penthouse A - Sleeps 11
Map1.4 mi from City Centre1300 yd from Michigan Avenue
FromUS$ 1 205 /nightSelect
Beautifully Remodeled Second Floor Flat In River North - 2N
Map1.5 mi from City Centre1300 yd from Michigan Avenue
FromUS$ 381 /nightSelect

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