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Chicago
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Illinois flight + hotel packages
Price found within the past 48 hours. Click for updated prices.
Hilton Chicago
Downtown Chicago
per person
Jan. 28 - Jan. 31
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Swissotel - Chicago
Downtown Chicago
per person
Jan. 28 - Jan. 31
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Virgin Hotels Chicago
Downtown Chicago
per person
Jan. 28 - Jan. 31
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a nightclub, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Viceroy Chicago
Downtown Chicago
per person
Mar. 9 - Mar. 14
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, an outdoor pool, and 2 restaurants. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pendry Chicago
Downtown Chicago
per person
Jan. 28 - Jan. 31
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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 Millennium Park are located nearby.
Top Illinois hotels deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $150 per night
CA $150
CA $176 total
includes taxes & fees
29 Dec - 30 Dec
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 Millennium Park are located nearby.
Free WiFi
Restaurant
River Hotel
75 East Wacker Drive, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $134 per night
CA $134
CA $157 total
includes taxes & fees
23 Jan - 24 Jan 2025
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
Hyatt Regency Chicago
151 East Wacker Dr, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $200 per night
CA $200
CA $277 total
includes taxes & fees
10 Jan - 11 Jan 2025
Book a stay at this eco-certified hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Free WiFi
Restaurant
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
350 West Wolf Point Plaza, Building 2, Chicago, IL
Free cancellation
The price is CA $159 per night
CA $159
CA $187 total
includes taxes & fees
7 Jan - 8 Jan 2025
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, 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.
Pool
Free WiFi
Eurostars Magnificent Mile
660 North State Street, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $138 per night
CA $138
CA $162 total
includes taxes & fees
5 Jan - 6 Jan 2025
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.
Spa
Free WiFi
Hilton Chicago
720 S Michigan Ave, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $201 per night
CA $201
CA $278 total
includes taxes & fees
4 Jan - 5 Jan 2025
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Pool
Pet-friendly
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
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.
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.
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.
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