Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
4.0-star property
Level Chicago - River North
Downtown Chicago
9.2/10 Wonderful! (1,011 reviews)
Jul 9 - Jul 12
3 night stay
Boston (BOS) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $887, price is now $556 per person
$556
per person
found 1 day ago
The pool area is fantastic. Rooms very ample-sized and comfortable. I would stay here again!
Reviewed on Jul 8, 2024
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (4,319 reviews)
Jul 7 - Jul 13
6 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Boston (BOS)
JetBlue Airways • Coach
Save 100% on your flight
Price was $1,675, price is now $993 per person
$993
per person
found 1 day ago
Great option! Great location! Great breakfast and friendly staff!
Reviewed on May 30, 2026
4.5-star property
Swissotel - Chicago
Downtown Chicago
9/10 Wonderful! (3,360 reviews)
Jul 7 - Jul 13
6 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Boston (BOS)
JetBlue Airways • Coach
Save 100% on your flight
Price was $1,232, price is now $732 per person
$732
per person
found 1 day ago
Great stay and we highly recommend. We will be back.
Reviewed on Apr 21, 2026
4.0-star property
Level Chicago Fulton Market
Downtown Chicago
9.2/10 Wonderful! (488 reviews)
Jul 7 - Jul 13
6 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Boston (BOS)
JetBlue Airways • Coach
Save 100% on your flight
Price was $1,547, price is now $947 per person
$947
per person
found 1 day ago
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (2,519 reviews)
Jul 13 - Jul 19
6 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Boston (BOS)
Southwest Airlines • Coach
Save 100% on your flight
Price was $1,912, price is now $1,222 per person
$1,222
per person
found 1 day ago
Really nice property, rooms were clean, and staff was extremely friendly
Reviewed on May 5, 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
The price is $173 total per night
$173 total
per night
Jun 29 - Jun 30
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
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Free Cancellation
1.07 mi from city center
The price is $183 total per night
$183 total
per night
Jun 28 - Jun 29
Guests of The Chicago Hotel Collection - Magnificent Mile enjoy features like a 24-hour gym, free WiFi in public areas, and express check-out. Self parking is available for USD 58 per night. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. Other amenities at this boutique hotel include a TV in a common area, wedding services, and a reception hall.
Pet friendly
Free WiFi
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Free Cancellation
Reserve now, pay when you stay
13.75 mi from city center
The price is $154 total per night
$154 total
per night
Jun 28 - Jun 29
At Hyatt Regency O'Hare Chicago, guests have access to a 24-hour gym, free WiFi in public areas, and meeting rooms. If you drive, self parking is USD 45 per night, or you can take advantage of the free airport shuttle (available 24 hours). Multilingual staff at the front desk are standing by 24/7 to help with luggage storage, securing valuables, and tours or tickets. Additional amenities include conference space, a business center, and a microwave in a common area.
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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