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Road Trips in Chicago

Anytime
1 guest
Anytime
1 guest

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • Condo
    • Cabin
    • House

  • Distance to center

    • 1 km
    • 2 km
    • 5 km

  • Rating

    • 4.5+
    • 4+

  • Booking Options

    • Instant Booking

  • Services

    • WiFi
    • Pool
    • Parking
    • Kitchen
    • TV
    • Air conditioning
    • Balcony/patio
    • Washing machine
    • Microwave
    • Hot tub
    • Fireplace
    • Dishwasher
    • Yard
    • Sauna
    • Crib
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • No pets
    • Wheelchair access

  • Activities

    • Grill
    • Fishing

Road Trips in Chicago: Recommended rentals

Road Trips in Chicago: find your perfect rental from just $80 per night!

House West Loop
Jul 20 - Jul 27
House ∙ 9 guests ∙ 3 bedrooms

Family-friendly vacation home with barbecue | City view | Pets allowed

West Loop, Chicago, Illinois, United States
$388
per night
Excellent(68 ratings)
$388
per night
View deal
Apartment Rush & Division
Apr 2 - Apr 9
Apartment ∙ 7 guests ∙ 3 bedrooms

Family-friendly rental apartment with terrace | Close to John Hancock Center | City view

Rush & Division, Chicago, Illinois, United States
$467
per night
Outstanding(7 ratings)
$467
per night
View deal
Condo Lincoln Park
Mar 18 - Mar 25
Condo ∙ 8 guests ∙ 5 bedrooms

Family-friendly condo with garden & patio

Lincoln Park, Chicago, Illinois, United States
$506
per night
Outstanding(37 ratings)
$506
per night
View deal
House Near North Side
Jul 26 - Aug 2
House ∙ 14 guests ∙ 3 bedrooms

Fully equipped house with terrace | City view

Near North Side, Chicago, Illinois, United States
$793
per night
Excellent(28 ratings)
$793
per night
View deal
Apartment Chicago Loop
Jul 5 - Jul 12
Apartment ∙ 6 guests ∙ 3 bedrooms

Rental apartment with patio & pool | Next to Cloud Gate | City view

Chicago Loop, Chicago, Illinois, United States
$538
per night
Outstanding(52 ratings)
$538
per night
View deal
House Goose Island
Jun 21 - Jun 28
House ∙ 14 guests ∙ 3 bedrooms

Children-friendly charming vacation home with sauna, patio & BBQ | City view | Perfect for remote work

Goose Island, Chicago, Illinois, United States
$340
per night
Outstanding(52 ratings)
$340
per night
View deal
Apartment Near North
Mar 18 - Mar 25
Apartment ∙ 7 guests ∙ 2 bedrooms

Holiday apartment with terrace | Near John Hancock Center | City view

Near North, Chicago, Illinois, United States
$142
per night
Good(22 ratings)
$142
per night
View deal
House Avalon Park
May 27 - Jun 3
House ∙ 10 guests ∙ 5 bedrooms

Children-friendly vacation home | Suitable for remote work

Avalon Park, Chicago, Illinois, United States
$469
per night
Outstanding(1 rating)
$469
per night
View deal
Condo Rogers Park
Apr 19 - Apr 26
Condo ∙ 8 guests ∙ 4 bedrooms

Fully equipped condo with garden, barbeque & jacuzzi | Nature view | Pets are welcome

Rogers Park, Chicago, Illinois, United States
$297
per night
Outstanding(246 ratings)
$297
per night
View deal
Apartment Streeterville
Mar 14 - Mar 21
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment with terrace | Near John Hancock Center | City view | Good for workation

Streeterville, Chicago, Illinois, United States
$309
per night
Excellent(38 ratings)
$309
per night
View deal
Apartment Washington Park
Mar 18 - Mar 25
Apartment ∙ 3 guests ∙ 3 bedrooms

Holiday apartment with barbeque & terrace | Suitable for remote work

Washington Park, Chicago, Illinois, United States
$103
per night
$103
per night
View deal
Apartment Heart of Chicago
May 27 - Jun 3
Apartment ∙ 10 guests ∙ 3 bedrooms

Fully equipped pleasant apartment with terrace

Heart of Chicago, Chicago, Illinois, United States
$439
per night
$439
per night
View deal
Condo Wrigleyville
Aug 8 - Aug 15
Condo ∙ 9 guests ∙ 4 bedrooms

Condo | Pet-friendly

Wrigleyville, Chicago, Illinois, United States
$592
per night
$592
per night
View deal
Condo Park West
-28%
Mar 18 - Mar 25
Condo ∙ 12 guests ∙ 4 bedrooms

Child-friendly spacious condo with garden | Suitable for remote work

Park West, Chicago, Illinois, United States
$811$597
per night
Outstanding(2 ratings)
$811$597
per night
View deal
House South Chicago
Apr 19 - Apr 26
House ∙ 5 guests ∙ 4 bedrooms

Charming house with 4 rooms for 5 persons

South Chicago, Chicago, Illinois, United States
$280
per night
$280
per night
View deal

Information about Road Trips in Chicago

😎 Least busy month March
🥳 Busiest month January
🛏️ Popular home types Apartment rental and House rental
🌡️ Hottest months 84 °F in July and August
❄️ Coldest months 17 °F in January and February
🌧️ Rainiest months March and April

Road Trips in Chicago: frequently asked questions

Road Trips in Chicago: What is the cost per night?

The average price for a vacation home in Chicago is usually between $133 and $719 per night.

Road Trips in Chicago: is there a good selection of vacation rentals for large groups?

Apartment rentals in Chicago should be considered for medium-sized groups and families, since they usually fit 5 guests.

Road Trips in Chicago: what kinds of vacation rentals can I book?

Sure, there are 653 House rentals and 2,399 Apartment rentals available in Chicago.

Average Nightly Rental Prices in Chicago

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Vacation Rental Price Information in Chicago

Vacation Rental Availability in Chicago

Rental availability information in Chicago

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Vacation rentals near Chicago with popular amenities

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