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Book Exclusive Chicago Vacation Packages

Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.
Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.
Save up to C$551 | Book Flight + Hotel at the same time^
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5
Save up to C$551 | Book Flight + Hotel at the same time^

Top Chicago Hotels Deals

Price for 1 night 2 adults*

C$146

31 Aug. - 1 Sep.

Per night/room

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5.0 85 East Wacker Drive, Chicago, IL
4.7/5
(28 Reviews)
Located in The Loop, this luxury hotel is steps away from Chicago Riverwalk and Michigan Avenue. Grant Park and Chicago Theatre are also within 10 minutes. Clark-Lake Station is 7 minutes by foot and State Station is 8 minutes.
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C$167

1 Sep. - 2 Sep.

Per night/room

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile

4.5 out of 5.0 20 E Chestnut St, Chicago, IL
4.7/5
(40 Reviews)
Located in Near North Side, this luxury hotel is within a 5-minute walk of State Street, Water Tower Place, and John Hancock Center. Chicago Water Tower and Michigan Avenue are also within 10 minutes. Chicago Station (Red Line) is only a 3-minute walk and Grand Station (Red Line) is 10 minutes.
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C$82

17 Aug. - 18 Aug.

Per night/room

Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5.0 1100 S Michigan Ave, Chicago, IL
4.1/5
(45 Reviews)
Located in The Loop, this hotel is within a 10-minute walk of Grant Park and Columbia College Chicago. Field Museum of Natural History and John G. Shedd Aquarium are also within 15 minutes. Roosevelt Station and Chicago Museum Campus-11th Street Station are within a 5-minute walk.
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Things to do in Chicago

See all 159 things to do in Chicago

#1Go Chicago Explorer Pass: Choose 3, 4 or 5 Top Attractions

Choose from Chicago's best attractions, guided tours, and experiences with the flexibility of an Go Chicago Explorer pass. Opt for a pass that's good for 3, ...

Duration 60d Free Cancellation Free Cancellation
4 of 5 (96 reviews)
The price now is
C$111
per adult
Go Chicago Explorer Pass: Choose 3, 4 or 5 Top Attractions

#2Architecture River Tour from Navy Pier

Equal parts boat and buildings, this river cruise gives you a from-the-water perspective of Chicago skyline and up-close views of its most iconic structures....

Duration 1h 15m+ Free Cancellation Free Cancellation
4.7 of 5 (312 reviews)
The price now is
C$54
per adult
Architecture River Tour from Navy Pier

#3Chicago CityPASS: Admission to Top 5 Chicago Attractions

Enjoy huge savings on admission to Chicago's must-see attractions with CityPASS mobile tickets. Take your time and enjoy each attraction, with up to 9 consec...

Free Cancellation Free Cancellation
4.7 of 5 (123 reviews)
Old priceC$293The price now is
C$146
per adult
Save!
Chicago CityPASS: Admission to Top 5 Chicago Attractions

#4360 CHICAGO Observation Deck (Hancock Centre)

At 360 CHICAGO, the guest experience begins at the ground floor with a museum-style exhibition celebrating Chicago’s history and nine of its culturally rich ...

Duration 14h Free Cancellation Free Cancellation
4.3 of 5 (135 reviews)
The price now is
C$34
per adult
360 CHICAGO Observation Deck (Hancock Centre)

Top Flight Deals to Chicago

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Thu., 8 Oct. - Mon., 12 Oct.
YTZ
Billy Bishop Toronto City
to
ORD
O'Hare Intl.
C$244

Roundtrip

found 2 days ago

Open YTZ to ORD flights search result page
Fri., 21 Aug. - Sat., 22 Aug.
YYZ
Pearson Intl.
to
ORD
O'Hare Intl.
C$254

Roundtrip

found 6 days ago

Open YYZ to ORD flights search result page
Mon., 21 Sep. - Thu., 1 Oct.
YUL
Pierre Elliott Trudeau Intl.
to
ORD
O'Hare Intl.
C$330

Roundtrip

found 5 days ago

Open YUL to ORD flights search result page

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^Savings based on all package bookings made with Flight + Hotel on Travelocity.com from January 1, 2019 to December 31, 2019, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.