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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
Max. 1 km
Max. 2 km
Max. 5 km
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

Best Vacation Home Deals in Chicago

House Jefferson Park
Jan 13 - Jan 20
-59%
$380
$157 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Jefferson Park with Yard
5.0
"Excellent" (36 ratings)
Jefferson Park, Chicago, Illinois, United States
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House West Loop
Jan 13 - Jan 20
-40%
$1,071
$643 per night
House ∙ 15 guests ∙ 4 bedrooms
Vacation Home in West Loop with Outdoor Terrace + Skyline Views
5.0
"Excellent" (47 ratings)
West Loop, Chicago, Illinois, United States
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Apartment Andersonville
Sep 9 - Sep 16
-26%
$227
$169 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Rental Apartment in Andersonville with Yard
5.0
"Excellent" (69 ratings)
Andersonville, Chicago, Illinois, United States
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Aparthotel Near North
Jan 13 - Jan 20
-35%
$428
$278 per night
Aparthotel ∙ 4 guests ∙ 1 bedroom
Aparthotel in Near North with Grill & Pool, Close to John Hancock Center
5.0
"Excellent" (184 ratings)
Near North, Chicago, Illinois, United States
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Apartment Lake View East
Mar 30 - Apr 6
-78%
$349
$78 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Rental Apartment in Lake View East
4.4
"Very good" (12 ratings)
Lake View East, Chicago, Illinois, United States
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Apartment Near North
Jan 6 - Jan 13
-66%
$601
$205 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
Apartment in Near North with On-Site Parking, Near John Hancock Center
4.9
"Excellent" (23 ratings)
Near North, Chicago, Illinois, United States
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House Avondale
Mar 27 - Apr 3
-76%
$1,321
$315 per night
House ∙ 14 guests ∙ 5 bedrooms
Pleasant House in Avondale with Grill & Yard
4.5
"Outstanding" (42 ratings)
Avondale, Chicago, Illinois, United States
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Apartment Near North
Jan 6 - Jan 13
-69%
$617
$192 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
Apartment in Near North with On-Site Parking, Close to John Hancock Center
4.9
"Excellent" (50 ratings)
Near North, Chicago, Illinois, United States
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Apartment University Village / Little Italy
Feb 3 - Feb 10
-44%
$355
$199 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
Historic Apartment in University Village / Little Italy
5.0
"Excellent" (68 ratings)
University Village / Little Italy, Chicago, Illinois, United States
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Road Trips in Chicago: Top Accommodations

Apartment Roscoe Village
Dec 2 - Dec 9
$181 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Family Friendly Rental Apartment in Roscoe Village with Grill & Yard
5.0
"Excellent" (153 ratings)
Roscoe Village, Chicago, Illinois, United States
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Apartment Logan Square
Jul 7 - Jul 14
$113 per night
Apartment ∙ 4 guests ∙ 3 bedrooms
Sunny Rental Apartment in Logan Square with Grill
4.6
"Outstanding" (41 ratings)
Logan Square, Chicago, Illinois, United States
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House Hollywood Park
Oct 14 - Oct 21
$260 per night
House ∙ 5 guests ∙ 2 bedrooms
Entire House in Hollywood Park with Free Parking
5.0
"Excellent" (10 ratings)
Hollywood Park, Chicago, Illinois, United States
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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
max.
Min.
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

Frequently Asked Questions

Road Trips in Chicago: What is the vacation rental cost in Chicago?

The average price for a vacation home in Chicago is between $206 and $473 per night.

Can I find a vacation rental for a group of guests for Road Trips in Chicago?

in Chicago, medium-sized groups and families should consider Apartment rental since they can fit 4 guests.

What types of vacation homes can i book for Road Trips in Chicago?

You can find 2,029 Apartment rental and 334 House rental for Road Trips in Chicago right here on HomeToGo.

Average Nightly Rental Prices in Chicago

Vacation Rental Price Information in Chicago

Vacation Rental Availability in Chicago

Rental Availability Information in Chicago

Other Popular Destinations for Road Trips

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