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

Kinzie Hotel
Downtown Chicago
Save 100% on your flight
per person
May 20 - May 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy room service, a fitness center, and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.


Pendry Chicago
Downtown Chicago
Save 100% on your flight
per person
May 20 - May 24
just found
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
per person
May 20 - May 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
May 20 - May 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Top Chicago hotels deals

River Hotel
75 East Wacker Drive, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $141 per night
CA $141
CA $165 total
includes taxes & fees
31 Mar - 1 Apr
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

L7 Chicago by LOTTE
225 N Wabash Ave, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $211 per night
CA $211
CA $248 total
includes taxes & fees
23 Mar - 24 Mar
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour 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

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $164 per night
CA $164
CA $192 total
includes taxes & fees
24 Mar - 25 Mar
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 Chicago Riverwalk and Soldier Field are located nearby.
Free WiFi
Restaurant

Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave, Rosemont, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $165 per night
CA $165
CA $188 total
includes taxes & fees
26 Mar - 27 Mar
Book a stay at this eco-certified hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rosemont Theatre and Allstate Arena are located nearby.
Free airport shuttle
Pet-friendly

The Westin Michigan Avenue Chicago
909 North Michigan Ave, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $169 per night
CA $169
CA $234 total
includes taxes & fees
22 Mar - 23 Mar
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

Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street, Chicago, IL
Free cancellation
The price is CA $147 per night
CA $147
CA $173 total
includes taxes & fees
23 Mar - 24 Mar
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Chicago Riverwalk and United Center 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 art scene in this vibrant area.

McCormick Place
4.5/5(141 reviews)
During your trip, find out what's happening at McCormick Place, a top convention center in Chicago. Discover the acclaimed art scene and notable monuments in this vibrant 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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