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Road Trips in Chicago

Anytime
1 guest
Anytime
1 guest

Road Trips in Chicago: Recommended rentals

Road Trips in Chicago: find your perfect rental from just $61 per night!

Apartment South Shore
-64%
Mar 7 - Mar 14
Free cancellation
Apartment ∙ 8 guests ∙ 3 bedrooms

Apartment with 3 Rooms for 8 Persons

South Shore, Chicago, Illinois, United States
$404$167
per night
Outstanding
$404$167
per night
View deal
Apartment Rush & Division
May 2 - May 9
Apartment ∙ 7 guests ∙ 3 bedrooms

Family-Friendly Rental Apartment with Terrace | Near John Hancock Center | City View

Rush & Division, Chicago, Illinois, United States
$949
per night
Outstanding(4 ratings)
$949
per night
View deal
House Near North Side
Oct 3 - Oct 10
House ∙ 14 guests ∙ 3 bedrooms

Fully Equipped House with Patio | City View

Near North Side, Chicago, Illinois, United States
$745
per night
Excellent(27 ratings)
$745
per night
View deal
House Goose Island
Jul 12 - Jul 19
House ∙ 14 guests ∙ 3 bedrooms

Family-Friendly Big House with Barbeque, Terrace & Sauna | City View | Perfect for Remote Work

Goose Island, Chicago, Illinois, United States
$229
per night
Outstanding(51 ratings)
$229
per night
View deal
House South Deering
May 2 - May 9
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home with Garden | Perfect for Remote Work

South Deering, Chicago, Illinois, United States
$365
per night
Outstanding(1 rating)
$365
per night
View deal
House Avalon Park
-24%
May 2 - May 9
House ∙ 10 guests ∙ 5 bedrooms

Family-Oriented House | Suitable for Remote Work

Avalon Park, Chicago, Illinois, United States
$496$490
per night
Outstanding(1 rating)
$496$490
per night
View deal
Apartment Chicago Loop
Jul 5 - Jul 12
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment with Terrace & Pool | Next to Cloud Gate | City View

Chicago Loop, Chicago, Illinois, United States
$353
per night
Outstanding(47 ratings)
$353
per night
View deal
Apartment South Austin
-52%
Jun 28 - Jul 5
Apartment ∙ 6 guests ∙ 3 bedrooms

Holiday Apartment | Suitable for Remote Work

South Austin, Chicago, Illinois, United States
$278$152
per night
Excellent(22 ratings)
$278$152
per night
View deal
House Fifth City
-31%
May 2 - May 9
House ∙ 5 guests ∙ 3 bedrooms

Children-Friendly Beautiful Vacation Home with Garden, Barbeque & Patio | Perfect for Remote Work

Fifth City, Chicago, Illinois, United States
$256$211
per night
Outstanding(18 ratings)
$256$211
per night
View deal
Apartment Washington Park
May 2 - May 9
Apartment ∙ 3 guests ∙ 3 bedrooms

Holiday Apartment with Barbeque & Patio | Good for Workation

Washington Park, Chicago, Illinois, United States
$130
per night
$130
per night
View deal
Apartment Near North Side
Oct 3 - Oct 10
Apartment ∙ 11 guests ∙ 3 bedrooms

Fully Equipped Apartment with Patio | City View

Near North Side, Chicago, Illinois, United States
$945
per night
Excellent(40 ratings)
$945
per night
View deal
House Streeterville
Feb 8 - Feb 15
House ∙ 4 guests ∙ 1 bedroom

Vacation Home | Close to John Hancock Center | City View

Streeterville, Chicago, Illinois, United States
$117
per night
Outstanding(1 rating)
$117
per night
View deal
House South Shore
Jul 19 - Jul 26
House ∙ 6 guests ∙ 3 bedrooms

Nice Vacation Home | Pet-Friendly

South Shore, Chicago, Illinois, United States
$70
per night
$70
per night
View deal
Apartment Logan Square
Jul 19 - Jul 26
Apartment ∙ 4 guests ∙ 3 bedrooms

Wonderful Holiday Apartment | Pet-Friendly

Logan Square, Chicago, Illinois, United States
$134
per night
Excellent(7 ratings)
$134
per night
View deal
House Noble Square
Feb 8 - Feb 15
House ∙ 12 guests ∙ 5 bedrooms

House with BBQ, Terrace & Yard | Nature View | Good for Workation

Noble Square, Chicago, Illinois, United States
$881
per night
Outstanding(98 ratings)
$881
per night
View deal

Information about Road Trips in Chicago

📏 Average home size 90 m²
💳 Highest rates in October
🛏️ Popular home types House rental and Apartment rental
🌡️ Hottest months 84 °F in July and August
❄️ Coldest months 17 °F in January and February
🌧️ Rainiest months 9 rainy days in 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 $122 and $609 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 632 House rentals and 2,298 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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