Book Exclusive Illinois Vacation Packages
Search vacation packages deals in Illinois's top destinations
Chicago
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Illinois flight + hotel packages
Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel
Price was CA $1,015, price is now CA $694 per person
CA $694
per person
Mar 5 - Mar 8
found 19 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to St. Louis (STL)
Book a stay at this business-friendly hotel in Wildwood. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Six Flags St. Louis and Skid Row are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,867, price is now CA $1,270 per person
CA $1,270
per person
Feb 18 - Feb 22
found 13 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Book a stay at this 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,153, price is now CA $811 per person
CA $811
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Virgin Hotels Chicago
Downtown Chicago
Price was CA $1,545, price is now CA $1,133 per person
CA $1,133
per person
Apr 1 - Apr 6
found 11 hours ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a nightclub, and a rooftop terrace. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,073, price is now CA $795 per person
CA $795
per person
Feb 18 - Feb 22
found 13 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Top Illinois hotels deals
Hilton Chicago
720 S Michigan Ave Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $193 per night
CA $193
CA $267 total
Jan 17 - Jan 18
includes taxes & fees
Book a stay at this 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 Millennium Park and Soldier Field are located nearby.
Pool
Hot tub
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $199 per night
CA $199
CA $268 total
Jan 17 - Jan 18
includes taxes & fees
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Pool
Spa
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $124 per night
CA $124
CA $146 total
Jan 18 - Jan 19
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
Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
Free cancellation
Reserve now, pay when you stay
Book a stay at this 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
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 $130 per night
CA $130
CA $153 total
Jan 19 - Jan 20
includes taxes & fees
Stay at this 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
Eurostars Magnificent Mile
660 North State Street Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $130 per night
CA $130
CA $153 total
Feb 9 - Feb 10
includes taxes & fees
Book a stay at this 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
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.
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 art scene.
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