Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
4.0-star property
La Banque Hotel
9.4/10 Exceptional! (469 reviews)
Jun 3 - Jun 6
3 night stay
Dallas (DFW) to Chicago (ORD)
Spirit Airlines • Coach
Chicago (ORD) to Dallas (DFW)
Frontier Airlines • Coach
Price was $608, price is now $371 per person
$371
per person
found 1 day ago
Beautiful boutique hotel with great staff!
Reviewed on Sep 16, 2022
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (3,495 reviews)
Jun 4 - Jun 7
3 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,232, price is now $661 per person
$661
per person
found 1 day ago
I recommend 100% Everything was good, the staff, room and the food. Also, it is located in a good area.
Reviewed on Jan 14, 2026
4.0-star property
Level Chicago – Old Town
Downtown Chicago
9/10 Wonderful! (441 reviews)
Jun 4 - Jun 8
4 night stay
Boston (BOS) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $1,458, price is now $896 per person
$896
per person
found 24 hours ago
We always love staying here. Such great service and nice accommodations.
Reviewed on Nov 20, 2025
4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
8.2/10 Very Good! (2,575 reviews)
Jun 4 - Jun 7
3 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $812, price is now $506 per person
$506
per person
found 1 day ago
The rooms were clean and smelled fresh.
Reviewed on Jan 8, 2026
4.5-star property
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (3,613 reviews)
May 25 - May 29
4 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,135, price is now $727 per person
$727
per person
found 1 day ago
Everything was perfect
Reviewed on Mar 9, 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
$101 nightly
The price is $118 total per night
$118 total
Apr 1 - Apr 2
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 concierge services, luggage storage, and dry cleaning/laundry. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.91 mi from city center
$156 nightly
The price is $183 total per night
$183 total
Mar 30 - Mar 31
Total with taxes and fees
A 24-hour gym and free WiFi in public areas are features at Hotel Riu Plaza Chicago. Multilingual staff at the 24-hour front desk can assist with luggage storage, dry cleaning/laundry, and concierge services.
Breakfast included
Free WiFi
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.83 mi from city center
$127 nightly
The price is $149 total per night
$149 total
Mar 22 - Mar 23
Total with taxes and fees
Guests of Embassy Suites by Hilton Chicago Downtown River North have access to an indoor pool, a gym, and WiFi in public areas. Valet parking is available for USD 79.00 per night. Multilingual staff at the front desk are standing by 24/7 to help with dry cleaning/laundry, concierge services, and luggage storage. Additional amenities include meeting rooms, conference space, and a business center.
Pool
Breakfast included
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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