Vacation rentals in Chicago, United States

Carefully selected & verified rentals in Chicago, United States
Check-in
26Jun2025Select date
Check-out
27Jun2025Select date
Rooms and Guests2 Guests, 1 Room
View map
181-200 out of 922
Sort by: high popularity
  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
The Haven, Great Location Near Downtown, Medical District And United Center Apartment Chicago
Map2.6 mi from City Centre1700 yd from United Center
FromUS$ 507 /nightSelect
Classic Chicago Edifice Near United Center And Downtown
Map2.6 mi from City Centre1700 yd from United Center
Select
Wonderful Room Close To Downtown Chicago - Free Parking
Map5.2 mi from City Centre500 yd from Lowe Park
FromUS$ 34 /nightSelect
Chicago North Shore Nest
Map8.9 mi from City Centre1300 yd from Loyola University Chicago
FromUS$ 99 /nightSelect
Luxe And Modern Chicago Condo - 7 Mi To Downtown!
Map5.6 mi from City Centre500 yd from Garfield (Green Line)
FromUS$ 324 /nightSelect
Stylish Studio Apartment In Portage Park - Pensacola 2N
Map8.3 mi from City Centre1000 yd from Montrose Station (Blue Line)
FromUS$ 169 /nightSelect
1Br Deluxe Apt With Complete Amenities - Campbell 3
Map6.7 mi from City Centre300 yd from Western Station (Brown Line)
FromUS$ 58 /nightSelect
Inviting 2-Bedroom Apt In Hyde Park - The Blackwood 0404
Map5.8 mi from City Centre
FromUS$ 276 /nightSelect
Group-Friendly 2Br With Optional Parking And Gym Access Near Mccormick Place And Soldier Field
Map1.7 mi from City Centre800 yd from McCormick Place
FromUS$ 509 /nightSelect
Ukrainian Village 2Br Modern Apartment D1
Map2.5 mi from City Centre1.2 mi from United Center
FromUS$ 224 /nightSelect
Spacious Historic Apartments In Lakeview Chicago - Walk To Wrigley, Nightlife, Shops, Hospitals
Map4.4 mi from City Centre1300 yd from Wrigley Field
FromUS$ 232 /nightSelect
Modern And Bright 2Br On Michigan Ave With Optional Parking And Gym Access Near Soldier Field & Grant Park
Map1.7 mi from City Centre800 yd from McCormick Place
FromUS$ 522 /nightSelect
Well-Appointed Cozy Portage Park Apt, Dogs, Kids, Free Parking, 420 Compliant
Map8.9 mi from City Centre700 yd from West Portage Park Ctr-The Arts
FromUS$ 101 /nightSelect
The Upscale Getaway Near Downtown
Map2.4 mi from City Centre1400 yd from United Center
FromUS$ 145 /nightSelect
3Br Elegant Glass Penthouse Pool With Deck & Gym
Map1400 yd from City Centre1200 yd from Chicago Union Station
FromUS$ 739 /nightSelect
Chateau De Woodlawn - Peaceful 3 Bedroom Apartment.
Map7.2 mi from City Centre800 yd from King Drive
FromUS$ 265 /nightSelect
Comfortable 2Br Chicago Apt - Sunnyside 2F
Map7.0 mi from City Centre400 yd from Kedzie Station (Brown Line)
FromUS$ 79 /nightSelect
Cozy & Inviting 2Br Apartment - Sunnyside 3F
Map7.0 mi from City Centre
FromUS$ 79 /nightSelect
1Br Vibrant & Inviting Apt In Chicago - Montrose 2E
Map8.1 mi from City Centre
FromUS$ 68 /nightSelect
Tiny House - Chicago Pilsen Neighborhood
Map2.7 mi from City Centre700 yd from Damen Station (Pink Line)
FromUS$ 171 /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