Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (2,606 reviews)
Oct 9 - Oct 12
3 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Boston (BOS)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,887, price is now $1,292 per person
$1,292
per person
found 1 day ago
Parking was way too expensive and hard to understand
Reviewed on Jul 31, 2026
4.0-star property
Eurostars Magnificent Mile
Downtown Chicago
9/10 Wonderful! (3,732 reviews)
Oct 8 - Oct 12
4 night stay
Boston (BOS) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $2,221, price is now $1,564 per person
$1,564
per person
found 1 day ago
Very, very expensive. Rooms are large, up-to-date, modern, and clean. Staff are polite and helpful; air conditioning works and is an upgrade.
Reviewed on Jul 31, 2026
4.0-star property
Level Chicago Fulton Market
Downtown Chicago
9.2/10 Wonderful! (540 reviews)
Oct 16 - Oct 19
3 night stay
Boston (BOS) to Chicago (ORD)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,136, price is now $822 per person
$822
per person
found 1 day ago
Comes with all the comforts of
Home.
Reviewed on Jul 29, 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
$142 nightly
The price is $169 total per night
$169 total
Aug 31 - Sep 1
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 dry cleaning/laundry, concierge services, and securing valuables. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Free Cancellation
Reserve now, pay when you stay
1.74 mi from city center
$152 nightly
The price is $181 total per night
$181 total
Aug 11 - Aug 12
Total with taxes and fees
Guests of The Chicago Hotel Collection Ambassador Gold Coast enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is offered for USD 75 per night. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. Additional amenities include conference space, express check-out, and a banquet 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
$169 nightly
The price is $193 total per night
$193 total
Aug 30 - Aug 31
Total with taxes and fees
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 tours or tickets, luggage storage, and dry cleaning/laundry. Additional amenities include conference space, a business center, and a microwave in a common area.
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: Willis Tower Skydeck and The Ledge Ticket
$36
per child
88% of travellers recommend
Chicago CityPASS®: Experience 5 must-see attractions
$144
per adult
94% of travellers recommend
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