
Book Exclusive Chicago Vacation Packages
Chicago flight + hotel packages
Price found within the past 48 hours. Click for updated prices.

Hyatt Centric The Loop Chicago
Downtown Chicago
per person
Jun. 27 - Jun. 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Art Institute of Chicago are located nearby.

Kimpton Gray Hotel by IHG
Downtown Chicago
Save 100% on your flight
per person
Jul. 18 - Jul. 22
found 7 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Art Institute of Chicago and Chicago Riverwalk are located nearby.

Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
per person
Jun. 20 - Jun. 27
found 23 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Level Chicago Fulton Market
Downtown Chicago
per person
Jul. 3 - Jul. 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Level Chicago - River North
Downtown Chicago
per person
Jul. 3 - Jul. 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Top Chicago hotels deals

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $177 per night
CA $177
CA $208 total
May 12 - May 13
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Art Institute of Chicago are located nearby.
Free WiFi
Restaurant

Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $236 per night
CA $236
CA $277 total
May 27 - May 28
includes taxes & fees
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pool
Breakfast included

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $230 per night
CA $230
CA $270 total
May 27 - May 28
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pet-friendly
Free WiFi

Warwick Allerton - Chicago
701 North Michigan Avenue, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $132 per night
CA $132
CA $189 total
May 27 - May 28
includes taxes & fees
Stay at this 4-star family-friendly hotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and in-room massages. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Air conditioning
Gym

The Westin Michigan Avenue Chicago
909 North Michigan Ave, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $219 per night
CA $219
CA $299 total
May 26 - May 27
includes taxes & fees
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Spa
Pet-friendly

River Hotel
75 East Wacker Drive, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $166 per night
CA $166
CA $195 total
May 27 - May 28
includes taxes & fees
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Pet-friendly
Free WiFi
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Popular places to visit

Wrigley Field
4.5/5(158 reviews)
Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.

Six Flags Great America
4.5/5(5 reviews)
Enjoy the excitement at Six Flags Great America and see why people love this theme park in Gurnee. Stroll along the lakeside or visit the shops in this family-friendly area.

Michigan Avenue
4.5/5(19 reviews)
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
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