Skip to main content
Flights
Hotels
Cars
Flight+Hotel
More
Vacations in Chicago
2 travellers
Travellers
Unfortunately, our partners limit offers to 6 travellers total. Please adjust your selection to continue.
Adults
2 adults selected
Children
0 children selected
Age Child 1
Under 2 years
Under 2 years
2 years
3 years
4 years
5 years
6 years
7 years
8 years
9 years
10 years
11 years
12 years
13 years
14 years
15 years
16 years
17 years
Age Child 2
Under 2 years
Under 2 years
2 years
3 years
4 years
5 years
6 years
7 years
8 years
9 years
10 years
11 years
12 years
13 years
14 years
15 years
16 years
17 years
Age Child 3
Under 2 years
Under 2 years
2 years
3 years
4 years
5 years
6 years
7 years
8 years
9 years
10 years
11 years
12 years
13 years
14 years
15 years
16 years
17 years
Continue
Boston (BOS)
Chicago
Thu. 14/7
Sun. 17/7
Search
Compare vs. KAYAK
all
|
none
Top vacations
Family
Romantic
Luxury
Budget
Chicago vacation information
Top vacation (Flight+Hotel)
C$ 682
Family vacation (Flight+Hotel)
C$ 619
Romantic vacation (Flight+Hotel)
C$ 721
Luxury vacation (Flight+Hotel)
C$ 714
Budget vacation (Flight+Hotel)
C$ 508
Most popular vacation deals in Chicago
Courtyard by Marriott Chicago Magnificent Mile
8.2
Excellent
374 reviews
C$ 2,135
3 nights + flight
View Deal
Stay in 'The Glen' Business District! Free Breakfast, Pool. | Staybridge
C$ 2,550
3 nights + flight
View Deal
Best Western Plus O'Hare International South Hotel
6.8
Good
389 reviews
C$ 1,144
3 nights + flight
View Deal
Summit Fhs Rental #2
C$ 2,895
3 nights + flight
View Deal
Staybridge Studio in 'The Glen' District w/ Free Breakfast! Indoor Pool, 24h Business Center.
C$ 2,018
3 nights + flight
View Deal
The Wicker Park Inn
8.4
Excellent
9 reviews
C$ 2,847
3 nights + flight
View Deal
Three Bedroom Apartment In Very Convenient Location!
10.0
Excellent
15 reviews
C$ 2,279
3 nights + flight
View Deal
1BR Staycation Getaway in Downtown Oak Park
C$ 2,306
3 nights + flight
View Deal
Safe and convenient
C$ 1,405
3 nights + flight
View Deal
Elegantly decorated spacious 4 bedroom, 5 bathroom home in historic Oak Park
10.0
Excellent
4 reviews
C$ 7,484
3 nights + flight
View Deal
View all deals
Other popular destinations
Miami Beach
Fort Lauderdale
Barcelona
Rome
Italy
Cozumel
San José del Cabo
Anguilla
Negril
Anaheim
Palm Springs
Cayo Coco
Honduras
Phoenix
Portugal
Boston
Arizona
Tampa
Key West
Florida
Flight+Hotel
Chicago
Thu. 14/7
Sun. 17/7
Choose up to 3 origin airports
Location
Airports within
100 km
50 km
100 km
200 km
300 km
Airport
Drive
Transit
Km
Pop.
Enter a location to see nearby airports
OK
Choose up to 3 airports
Enter a location to see nearby airports
OK
Thu. 14/7
Thu. 21/7
Choose up to 3 origin airports
Location
Airports within
100 km
50 km
100 km
200 km
300 km
Airport
Drive
Transit
Km
Pop.
Enter a location to see nearby airports
OK
Choose up to 3 airports
Enter a location to see nearby airports
2 travellers
Travellers
Unfortunately, our partners limit offers to 6 travellers total. Please adjust your selection to continue.
Adults
2 adults selected
Children
0 children selected
Age Child 1
Under 2 years
Under 2 years
2 years
3 years
4 years
5 years
6 years
7 years
8 years
9 years
10 years
11 years
12 years
13 years
14 years
15 years
16 years
17 years
Age Child 2
Under 2 years
Under 2 years
2 years
3 years
4 years
5 years
6 years
7 years
8 years
9 years
10 years
11 years
12 years
13 years
14 years
15 years
16 years
17 years
Age Child 3
Under 2 years
Under 2 years
2 years
3 years
4 years
5 years
6 years
7 years
8 years
9 years
10 years
11 years
12 years
13 years
14 years
15 years
16 years
17 years
Continue
Boston (BOS)
To
Thu. 14/7
Thu. 21/7
Search
Compare vs. KAYAK
all
|
none
products - flights
interface - City
products - hotels
interface - POI
interface - map
Star