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Road Trips in Chicago

Chicago
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Distance to center
1 km
2 km
5 km
Rating
4.5+
4+
3.5+

Best Vacation Home Deals in Chicago

House Washington Park
Jan 13 - Jan 20
-58%
$730
$306 per night
House ∙ 8 guests ∙ 3 bedrooms
House in Washington Park with Yard
Washington Park, Chicago, Illinois, United States
Details
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Condo West Lakeview
Jan 20 - Jan 27
-61%
$381
$148 per night
Condo ∙ 9 guests ∙ 3 bedrooms
Condo in West Lakeview
4.4
Very good (3 ratings)
West Lakeview, Chicago, Illinois, United States
Details
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Condo The Gap
Jan 6 - Jan 13
-24%
$124
$95 per night
Condo ∙ 5 guests ∙ 2 bedrooms
Condo in The Gap
3.6
Good (27 ratings)
The Gap, Chicago, Illinois, United States
Details
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Apartment Heart of Chicago
Jan 6 - Jan 13
-55%
$218
$98 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
Entire Apartment in Heart Of Chicago
5.0
Outstanding (50 ratings)
Heart of Chicago, Chicago, Illinois, United States
Details
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House Avondale
Jan 19 - Jan 26
-59%
$879
$358 per night
House ∙ 14 guests ∙ 5 bedrooms
Pleasant House in Avondale with Grill & Yard
4.6
Excellent (47 ratings)
Avondale, Chicago, Illinois, United States
Details
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House Grand Boulevard
Oct 28 - Nov 4
-15%
$244
$207 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Grand Boulevard
5.0
Outstanding (3 ratings)
Grand Boulevard, Chicago, Illinois, United States
Details
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House The Island
Dec 9 - Dec 16
-28%
$145
$104 per night
House ∙ 8 guests ∙ 3 bedrooms
Wonderful Vacation Home in The Island with Yard
4.5
Excellent (17 ratings)
The Island, Chicago, Illinois, United States
Details
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House Logan Square
Jan 20 - Jan 27
-19%
$435
$350 per night
House ∙ 10 guests ∙ 5 bedrooms
Wonderful House in Logan Square with Grill
3.8
Good (5 ratings)
Logan Square, Chicago, Illinois, United States
Details
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House Logan Square
Jan 6 - Jan 13
-55%
$288
$129 per night
House ∙ 10 guests ∙ 2 bedrooms
Nice Vacation Home in Logan Square with Free Parking
4.5
Excellent (194 ratings)
Logan Square, Chicago, Illinois, United States
Details
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Road Trips in Chicago: Top Accommodations

Apartment Washington Park
Mar 9 - Mar 16
$99 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Apartment in Washington Park
Washington Park, Chicago, Illinois, United States
Details
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House West Town
Mar 2 - Mar 9
$175 per night
House ∙ 8 guests ∙ 3 bedrooms
Nice House in West Town
4.5
Excellent (14 ratings)
West Town, Chicago, Illinois, United States
Details
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House Avondale
Jan 19 - Jan 26
-59%
$879
$358 per night
House ∙ 14 guests ∙ 5 bedrooms
Pleasant House in Avondale with Grill & Yard
4.6
Excellent (47 ratings)
Avondale, Chicago, Illinois, United States
Details
Vrbo
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The Weather in Chicago

max.
Min.
31°
17°
8 days 8
max.
Min.
35°
20°
7 days 7
max.
Min.
45°
29°
9 days 9
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59°
40°
9 days 9
max.
Min.
70°
50°
8 days 8
max.
Min.
81°
60°
9 days 9
max.
Min.
84°
65°
8 days 8
max.
Min.
83°
64°
8 days 8
max.
Min.
76°
56°
8 days 8
max.
Min.
65°
46°
7 days 7
max.
Min.
48°
33°
8 days 8
max.
Min.
35°
22°
9 days 9
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Information about Road Trips in Chicago

😎 Least busy month October
🥳 Busiest month August
🛏️ Popular home types House rental and Apartment rental
🌡️ Hottest months July and August
❄️ Coldest months January and February
🌧️ Rainiest months 9 rainy days in March and April

Frequently Asked Questions

What types of vacation homes are available for Road Trips in Chicago?

There is a lot of House rental and Apartment rental that are great for Road Trips in Chicago.

Road Trips in Chicago: How much does it cost to rent a vacation home in Chicago?

HomeToGo offers ideal rentals for Road Trips in Chicago, with prices as low as $60 per night.

Can I find a vacation home for a group for Road Trips in Chicago?

The average size for a Apartment rental is 81 m² and can fit 4 guests on average which is ideal for medium-sized groups and families.

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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