Vacation Rentals in Chicago

Vacation Rentals in Chicago

Start comparing over 612 rentals in Chicago and book at the best price!

Find Vacation Rentals in Chicago

Highlights Chicago

  • World class galleries and museums
  • Sporting spectacles
  • Beautiful skyline
  • Lakefront setting
  • Good public transportation
  • Shopping

Best Vacation Rentals in Chicago

Guests agree: these stays are highly rated for location, cleanliness, and more.
Vacation Rental for 5 Guests in Chicago, Cook County
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Chicago, Cook County
Vacation Rental • 5 Guests • 2 Bedrooms
- Skyline views + private balcony - Sleep 5: 2 Queen bedrooms + single rollaway bed; 2 baths - Pack 'n Play by request - Sonos sound system + Smart TVs - Fully-Equipped Chef's Kitchen + Complimentary Nespresso & Tea - Social club with gaming center, large island and bar seating (building) - 5 min to Magnificent Mile; 10 min to Lincoln Park Zoo - Parking $50/night (spots are limited, so ask when you book to check availability) - Check-in 4 pm (same-day 6 pm), check-out 11 am - $1000 refundable deposit via credit card; gov’t ID + standard background check for all adults Check your dates n...
from $227 / night
Vacation Rental for 5 Guests in Chicago, Cook County
Vacation Rental for 5 Guests in Chicago, Cook County, Picture 1
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Chicago, Cook County
Vacation Rental • 5 Guests • 2 Bedrooms
- Top-floor views + spacious living area - Sleep 5: 2 Queen beds + rollaway; 2 baths - Pack & Play available - Fully-Equipped Chef's Kitchen + Complimentary Nespresso & Tea - Sonos sound system + 2 Smart TVs - 2,600 sq ft Health Club (building) - 5 min to the Magnificent Mile; 8 min to Oak Street Beach - Parking $50/night (spots are limited, so ask when you book to check availability) - Check-in 4 pm (same-day 6 pm), check-out 11 am - $1000 refundable deposit via credit card; gov’t ID + standard background check for all adults Check your dates now—this prime location books fast.
from $230 / night
Vacation Rental for 6 Guests in Chicago, Cook County
Vacation Rental for 6 Guests in Chicago, Cook County, Picture 1
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Chicago, Cook County
Vacation Rental • 6 Guests • 2 Bedrooms
10.0
(7 reviews)
- Top-floor skyline views + modern open layout - Sleep 6: 2 Queen rooms; 1 single rollaway bed; 1 futon; 2 baths - Pack & Play by request - 75" TV + Sonos sound system - Designer Kitchen + Premium Stainless Steel Appliances & Nespresso - Fully-Equipped Fitness Center (building) - 4 min to Union Station; 8 min to Willis Tower - Parking $50/night (spots are limited, so ask when you book to check availability) - Check-in 4 pm (same-day 6 pm), check-out 11 am - $1000 refundable deposit via credit card; gov’t ID + standard background check for all adults Check your dates now—this sought-...
from $214 / night

Other holiday ideas and property types in Chicago that might be interesting

Popular Destinations in Chicago

    Prices and availability

    Current Vacation rental prices in Chicago

    $529for 1 Nov - 8 Nov
    $523 annual average
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    Average price per week

    Current vacation rental availability in Chicago

    12%for 1 Nov - 8 Nov
    37% annual average
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    Percentage of available rentals

    Chicago Vacation Rentals

    Elegant City Center Vacation Homes

    America’s third largest city, Chicago is full of wonderful vacation rental options. For example, if you look inside the Loop, you’ll find plenty of upscale apartment properties, with multiple bathrooms, bedrooms and huge living areas – all within walking distance of the subway and major attractions.

    Choose a Lakefront Vacation Home or a Suburban Villa

    You don’t need to stay in the center of Chicago. One of the great things about the city is the beautiful shorefront of Lake Michigan. Check out lakefront neighborhoods like Lincoln Park, the Near North Side or Gold Coast. Or look inland to roomy vacation rental options in affluent suburbs like Wheaton or Itasca. There’s no shortage of fantastic accommodation possibilities in the Windy City.

    Downtown Chicago
    Downtown Chicago
    The famous Route 66 highway begins right outside the doors of the Art Institute of Chicago

    Top 5 things to do in Chicago

    1. Visit the city’s huge number of museums

    Chicago’s museum collection is incredible. The Field Museum is a massive natural history center, the Art Institute hosts a huge collection of modern art, the Chicago History Museum teaches visitors about the city’s fascinating past, while the Science Museum immerses guests in the world of technology.

    2. Ascend to the panoramic deck of the John Hancock Center

    There’s no better place to witness the breathtaking skyline of Chicago than the observation deck of the soaring John Hancock Tower, which is accessible by a high-speed elevator (which is an attraction in itself). Be sure to take your camera.

    3. Explore the Chicago Riverwalk

    The south bank of the Chicago River has been turned into one of America’s finest urban walkways, with attractions like tiki bars, birdwatching tours, water taxis, wine bars and brewery pubs dotted along its route.

    4. Try a Chicago deep dish pizza

    Deep dish pizza is one of Chicago’s culinary specialties. If you want to try a slice, head to local institutions like Pequod’s, the Art of Pizza or Giordano’s for a pizza pie that you will never forget.

    5. Head to Soldier Field, Wrigley Field or the United Center for sporting action

    Chicago’s teams are all in the top bracket of their sports, so whether you love NFL, NBA, Major League Baseball or even soccer or hockey, be sure to catch a contest during your stay.