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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,089, price is now CA $738 per person
CA $738
per person
Sep 21 - Sep 24
just found
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,386, price is now CA $925 per person
CA $925
per person
Sep 21 - Sep 24
just found
Roundtrip flight included
Detroit (DTW) 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.
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,264, price is now CA $1,571 per person
CA $1,571
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Regina (YQR) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Holiday Inn Chicago O'Hare – Rosemont by IHG
Price was CA $1,526, price is now CA $1,062 per person
CA $1,062
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Allstate Arena and Rivers Casino are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,785, price is now CA $1,270 per person
CA $1,270
per person
Sep 21 - Sep 24
just found
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue 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 $146 per night
CA $146
CA $173 total
Sep 8 - Sep 9
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $199 per night
CA $199
CA $237 total
Aug 30 - Aug 31
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $225 per night
CA $225
CA $312 total
Sep 10 - Sep 11
includes taxes & fees
Book a stay at this business-friendly 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 Millennium Park are located nearby.
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Free cancellation
Reserve now, pay when you stay
The price is CA $236 per night
CA $236
CA $269 total
Aug 30 - Aug 31
includes taxes & fees
Book a stay at this business-friendly 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 Fashion Outlets of Chicago are located nearby.
Hilton Chicago
720 S Michigan Ave Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $236 per night
CA $236
CA $321 total
Sep 8 - Sep 9
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 Grant Park and Millennium Park are located nearby.
Fairmont Chicago at Millennium Park
200 North Columbus Drive Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $361 per night
CA $361
CA $479 total
Sep 2 - Sep 3
includes taxes & fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
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.
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