Chicago Vacation Packages
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Top Chicago vacation package deals
Price found within the past 48 hours. Click for updated prices.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.6/10 Exceptional! (1,986 reviews)
Nov 5 - Nov 8
3 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,559, price is now $978 per person
$978
per person
found 1 day ago
隔音效果差
Reviewed on Aug 27, 2026
5.0-star property
The Langham, Chicago
Downtown Chicago
9.8/10 Exceptional! (1,004 reviews)
Nov 9 - Nov 12
3 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,903, price is now $1,230 per person
$1,230
per person
found 1 day ago
The bestof Chicago
Reviewed on Aug 26, 2026
4.0-star property
Level Chicago - River North
Downtown Chicago
9.2/10 Wonderful! (1,055 reviews)
Oct 16 - Oct 19
3 night stay
Boston (BOS) to Chicago (ORD)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,205, price is now $781 per person
$781
per person
found 24 hours ago
I would like to come back it’s safe and clean u can see the view
Reviewed on Aug 26, 2026
4.0-star property
Level Chicago Fulton Market
Downtown Chicago
9.2/10 Wonderful! (550 reviews)
Oct 16 - Oct 19
3 night stay
Boston (BOS) to Chicago (ORD)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,184, price is now $786 per person
$786
per person
found 24 hours ago
Great! But parking was bad.
Reviewed on Aug 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
$115 nightly
The price is $136 total per night
$136 total
Sep 8 - Sep 9
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
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
$143 nightly
The price is $170 total per night
$170 total
Aug 31 - Sep 1
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 wedding services.
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
$232 nightly
The price is $272 total per night
$272 total
Sep 18 - Sep 19
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, securing valuables, and luggage storage. 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: Willis Tower Skydeck and The Ledge Ticket
$47
per adult
88% of travellers recommend
Chicago CityPASS®: Experience 5 must-see attractions
$144
per adult
94% of travellers recommend
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