Vacation rentals in Chicago, United States

Carefully selected & verified rentals in Chicago, United States
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Check-out
27Aug2025Select date
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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Chic Urban Gem In Logan Square Apartment Chicago
Map5.2 mi from City Centre900 yd from Roosevelt University Logan SQ
FromUS$ 165 /nightSelect
Apt 5 Mi To Chicago Loop Walk To Public Transit!
Map3.8 mi from City Centre500 yd from Kedzie-Homan
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Villa Vista
Map5.9 mi from City Centre1700 yd from Wrigley Field
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Luxurious 3Bd Penthouse L Private Patio L Gym L Stunning Rooftop
Map1.6 mi from City Centre100 yd from Chicago Station (Blue Line)
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Regal Stylish Uptown Loft Beachfront Rooftopwfhgym
Map6.5 mi from City Centre200 yd from Lawrence
FromUS$ 345 /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
4-star hotels
US$ 279
Apartments
US$ 306

Top vacation homes in Chicago

Based on guest reviews from the past 12 months

Vibrant Wrigleyville Escapes:
Cultural Hotspots in Little Italy:
Convenient Airport Access:
Days Inn Melrose Park/O'Hare South
Homey Retreats in the City:
5430 Happy Home
Urban Living with Style:

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

Which vacation rentals in Chicago are best for families with children?
Properties like 'Wrigley Oasis! Steps From The Field! - 3Bd 1Ba' and 'Wrigleyville Friends Unit - 5Bdrm' are spacious and family-friendly with amenities to accommodate larger groups.
Which vacation rentals in Chicago are located close to major attractions?
The 'Double Play Wrigley - Prime Location! - 1 Min Walk To Wrigley Field' is conveniently located near Wrigley Field. Similarly, 'Chicago 2Br Suite Perfect For Convention And Business Trips' is near McCormick Place and other central attractions.
Are there any vacation rentals in Chicago suited for couples looking for a romantic getaway?
Consider 'Chic Retreat | Fully Equipped Cozy 4/5 Br' or 'Stunning Duplex Condo #1 - Downtown River North' for a cozy yet upscale romantic experience, offering privacy and stylish design.

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
26Aug2025Select date
Check-out
27Aug2025Select date
Rooms and Guests2 Guests, 1 Room