Vacation rentals in Chicago, United States

Carefully selected & verified rentals in Chicago, United States

Check-in
30Jul
Check-out
31Jul
Rooms and Guests2 Guests, 1 Room
Chicago boasts attractions like Millennium Park, Navy Pier, and the Art Institute of Chicago. You can also catch a game at Wrigley Field or enjoy the waterfront at Oak Street Beach. Many options await you, from boutique hotels in the West Loop to hotels with pools and pet-friendly hotels scattered throughout the city. This selection includes the best Marriott Hotels, Wyndham Hotels, and IHG Hotels for fantastic stays. Book early, especially during festivals, and use the Blue Line train to navigate easily.
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1-20 out of 584
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  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
8.0
Great
Lincoln Park 3 Bedroom Penthouse
Map3.8 mi from City Centre
FromUS$ 234 /nightSelect
Luxury Chicago Suite
Map7.7 mi from City Centre
FromUS$ 173 /nightSelect
Chic Retreat
Map10.8 mi from City Centre
FromUS$ 292 /nightSelect
7.0
Very good
Wrigley Oasis! Steps From The Field! - 3Bd 1Ba
Map4.9 mi from City Centre500 yd from Wrigley Field
FromUS$ 457 /nightSelect
The Lyons' Lair
Map5.8 mi from City Centre1.2 mi from Wrigley Field
FromUS$ 273 /nightSelect
Experience Downtown Chicago At Millennium - Luxury Apartments In The Loop
Map1000 yd from City Centre300 yd from CIBC Theatre
FromUS$ 259 /nightSelect
Cozy & Near Downtown & Hyde Park
Map8.6 mi from City Centre
FromUS$ 103 /nightSelect
Retro 2 Bedroom Home 6 Mins To United Center With Parking
Map4.2 mi from City Centre
FromUS$ 334 /nightSelect
La Villita - Gateway To Chicago
Map3.9 mi from City Centre
FromUS$ 215 /nightSelect
8.0
Great
Hyde Park Modern Private Room - Near Univ Of Chicago
Map5.1 mi from City Centre
FromUS$ 111 /nightSelect
Beautiful Big 3 Bedroom Quiet Apt Near Downtown
Map9.1 mi from City Centre
FromUS$ 369 /nightSelect
Avenir West Loop Penthouses With Iconic City Views
Map1.5 mi from City Centre
FromUS$ 354 /nightSelect
6.2
Nice
Modern 2Br In South Loop Near Soldier Field, Grant Park, Downtown, & Lakefront Trail
Map1.7 mi from City Centre800 yd from McCormick Place
FromUS$ 446 /nightSelect
Condo Apartment Near Midway Airport
Map7.7 mi from City Centre
FromUS$ 150 /nightSelect
8.6
Great
Wrigley Garden Unit
Map4.8 mi from City Centre700 yd from Wrigley Field
FromUS$ 303 /nightSelect
Modern 3 Bedroom Close To Downtown Chicago
Map3.9 mi from City Centre
FromUS$ 87 /nightSelect
Walk To Wrigley 3Br1Ba Sleeps 8 Free Parking
Map4.4 mi from City Centre1300 yd from Wrigley Field
FromUS$ 601 /nightSelect
Stunning 2 Floor Penthouse Downtown
Map1.9 mi from City Centre
FromUS$ 557 /nightSelect
Foundry Unmatched Skyline Views At Lincoln Park
Map2.3 mi from City Centre
FromUS$ 977 /nightSelect
Game Day Getaway - 3Br In Vibrant Wrigleyville
Map5.3 mi from City Centre700 yd from Wrigley Field
FromUS$ 252 /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
USD 5 808
⬇️ The lowest price
USD 32
💸 Average price for
Apartments
USD 525

Top vacation homes in Chicago

Based on guest reviews from the past 12 months

How to get to Chicago

Explore local transportation options with ease

Airports
Chicago O'Hare International (ORD)
Midway International (MDW)

FAQs about Chicago rentals

Get answers to common questions and plan your adventure smoothly

What are the cheapest vacation rental options in Chicago?
Affordable choices include properties like 'Cozy 1 Bedroom, 1 Min From Irving Park Blue Line, Free Parking' and 'Convenient & Newly Decorated 1Br Apartment - Roscoe 1D', which typically range from $80 to $120 per night.

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.

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