Chicago Vacation Packages
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Top Chicago vacation package deals
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
8.2/10 Very Good! (2,797 reviews)
Sep 2 - Sep 7
5 night stay
Baltimore (BWI) to Chicago (ORD)
United • Coach
Chicago (ORD) to Baltimore (BWI)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,115, price is now $711 per person
$711
per person
found 1 day ago
Rooms were very old. There was blk mold or something in the shower. Window was broken too.
Reviewed on Jul 1, 2026
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (4,518 reviews)
Sep 2 - Sep 7
5 night stay
Baltimore (BWI) to Chicago (ORD)
United • Coach
Chicago (ORD) to Baltimore (BWI)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,634, price is now $991 per person
$991
per person
found 1 day ago
Highly recommend
Reviewed on Jul 1, 2026
4.0-star property
Level Chicago Fulton Market
Downtown Chicago
9.2/10 Wonderful! (504 reviews)
Sep 2 - Sep 7
5 night stay
Baltimore (BWI) to Chicago (ORD)
United • Coach
Chicago (ORD) to Baltimore (BWI)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,628, price is now $1,025 per person
$1,025
per person
found 1 day ago
Staff was super friendly. The room was perfect and the view was exceptional.
Would definitely stay here again.
Reviewed on Jun 27, 2026
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (2,554 reviews)
Sep 2 - Sep 7
5 night stay
Baltimore (BWI) to Chicago (ORD)
United • Coach
Chicago (ORD) to Baltimore (BWI)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,909, price is now $1,271 per person
$1,271
per person
found 1 day ago
Great stay; fabulous location, amazing views and access to so much; friendly staff. Super friendly and accommodating housekeeping! Food/bar service took a long long time, every time..long wait to order…long wait to get drinks…long wait to pay bill. Not enough staff behind the bar.
Reviewed on Jun 30, 2026
4.0-star property
Level Chicago – Old Town
Downtown Chicago
9/10 Wonderful! (495 reviews)
Sep 9 - Sep 12
3 night stay
Baltimore (BWI) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,148, price is now $767 per person
$767
per person
found 1 day ago
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 2026
Top rated hotels for your Chicago vacation package
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.43 mi from city center
$149 nightly
The price is $177 total per night
$177 total
Jul 2 - Jul 3
Total with taxes and fees
Guests of Congress Plaza Hotel enjoy a gym, free WiFi in public areas, and meeting rooms. Self parking is offered for USD 62.00 per night. Multilingual staff at the front desk are standing by 24/7 to help with securing valuables, concierge services, and luggage storage. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.98 mi from city center
$181 nightly
The price is $215 total per night
$215 total
Jul 5 - Jul 6
Total with taxes and fees
Guests of Omni Chicago Hotel have access to a 24-hour gym, in-room fitness, and free WiFi in public areas. Valet parking is offered for USD 89.49 per night. The 24-hour front desk has staff standing by to help with tours or tickets, dry cleaning/laundry, and securing valuables. Other amenities at this luxury hotel include conference space, express check-out, and a gift shop.
Pet friendly
Free WiFi
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Free Cancellation
Reserve now, pay when you stay
15.67 mi from city center
$240 nightly
The price is $282 total per night
$282 total
Jul 4 - Jul 5
Total with taxes and fees
Guests of Hilton Chicago O'Hare Airport enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is USD 77 per day if you plan to drive, or hop aboard the free airport shuttle (available on request). Multilingual staff at the front desk are standing by 24/7 to help with concierge services, luggage storage, and securing valuables. Additional amenities include a conference center, a business center, and a computer station.
Free airport shuttle
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.
Things to do
Chicago CityPASS®: Experience 5 must-see attractions
$144
per adult
94% of travellers recommend
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