Vacation Rentals in Chicago, United States from 29$/Night | Comfort & Style

Chicago

241-260 out of 922

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Urban Oasis - Great For Families With Kids Apartment Chicago

Map1.3 mi from City Centre

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Luxurious Lincoln Park Home With Gourmet Kitchen Chicago

Map3.7 mi from City Centre900 yd from Diversey

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Luxury 2Bd-2Ba View-Gym-Rooftop

Map1.6 mi from City Centre100 yd from Chicago Station (Blue Line)

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River N 1Br W Gym Pool Nr Magnificent Mile Chi-125

Map1.4 mi from City Centre400 yd from Michigan Avenue

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15Mins Dt Wicker Park Gem Sleeps 7 Freepark

Map2.8 mi from City Centre1.1 mi from United Center

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Luxury 1Br Michigan Suite Near Mccormick Parking

Map1.6 mi from City Centre700 yd from McCormick Place

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Stylish Humboldt Park Retreat - Walk To Parks & Easy Transit!

Map4.9 mi from City Centre

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Pool Table Free Parking Sleeps 8

Map1.4 mi from City Centre1.2 mi from Chicago Riverwalk

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Billiards Patio Parking

Map3.1 mi from City Centre

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2Br Near Ohare And Transit Newly Furnished Modern

Map12.5 mi from City Centre

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Blueground Greektown Bbq Gym Nr Willis Tower Chi-1254

Map900 yd from City Centre700 yd from Chicago Union Station

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3 Bedroomin The Medical Center

Map1.3 mi from City Centre1700 yd from United Center

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Rooftop West Loop Chicago

Map1.4 mi from City Centre1.1 mi from United Center

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South Loop 2 Bedroom Apt

Map1.0 mi from City Centre1100 yd from Grant Park

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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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Blueground Greektown Bbq Gym Nr Willis Tower Chi-1253

Map900 yd from City Centre700 yd from Chicago Union Station

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Ace Properties

Map6.2 mi from City Centre

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Amazing Place To Stay Near Downtown Chicago!

Map5.4 mi from City Centre

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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

💸 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.