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Chicago

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Chicago

Illinois flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 21 - Jul. 28
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby. Discover genuine guest reviews for Pendry Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 21 - Jul. 28
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Popular attractions Millennium Park and Chicago Riverwalk are located nearby. Discover genuine guest reviews for Fairmont Chicago at Millennium Park Gold Experience, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Sonesta Simply Suites Chicago O'Hare Airport

Sonesta Simply Suites Chicago O'Hare Airport

2.5 out of 5
O'Hare
per person
Jul. 10 - Jul. 16
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this business-friendly hotel in Schiller Park. Enjoy free WiFi, a free airport shuttle, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and Fashion Outlets of Chicago are located nearby. Discover genuine guest reviews for Sonesta Simply Suites Chicago O'Hare Airport, in O'Hare neighborhood, along with the latest prices and availability – book now.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 10 - Jun. 14
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 and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby. Discover genuine guest reviews for Level Chicago - River North, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 18 - Jul. 22
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby. Discover genuine guest reviews for Trump International Hotel & Tower Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.

Top Illinois hotels deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $207 per night
CA $207
per night
May 13 - May 14
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. Discover genuine guest reviews for Congress Plaza Hotel, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $220 per night
CA $220
per night
May 12 - May 13
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. Discover genuine guest reviews for River Hotel, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $192 per night
CA $192
per night
May 15 - May 16
Stay at this family-friendly hotel in Chicago. Enjoy WiFi, a 24-hour fitness center, and valet parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby. Discover genuine guest reviews for Warwick Allerton - Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $233 per night
CA $233
per night
May 12 - May 13
Stay at this 4-star spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a 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. Discover genuine guest reviews for Eurostars Magnificent Mile, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $159 per night
CA $159
per night
May 9 - May 10
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, breakfast, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby. Discover genuine guest reviews for Aloft Chicago Mag Mile, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $183 per night
CA $183
per night
May 12 - May 13
Stay at this 4-star boutique hotel in Chicago. Enjoy a 24-hour health club, onsite parking, 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. Discover genuine guest reviews for Hotel Felix River North/Magnificent Mile, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
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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

Image for Wrigley Field

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.

Wrigley Field
Image for McCormick Place

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.

McCormick Place
Image for Navy Pier

Navy Pier

4.5/5(459 reviews)

With a visit to Navy Pier, a favorite shopping spot in Chicago, you can enjoy some retail therapy. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

Navy Pier