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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921-922 out of 922
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Cosy Room Near Medical District With Private Balcony Chicago
Map3.0 mi from City Centre1000 yd from Western Station (Forest Park Branch)
FromUS$ 49 /nightSelect
Spacious Room By Medical District & Uic Chicago
Map3.0 mi from City Centre1000 yd from Western Station (Forest Park Branch)
FromUS$ 74 /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