Chicago Vacation Packages
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Top Chicago vacation package deals
Price found within the past 48 hours. Click for updated prices.
2.5-star property
Holiday Inn Chicago – Midway Airport S by IHG
West Lawn
8.2/10 Very Good! (1,022 reviews)
Oct 6 - Oct 12
6 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,018, price is now $711 per person
$711
per person
found 1 day ago
Everything was fine however the parking price was expensive.
Reviewed on Aug 2, 2026
4.5-star property
Pendry Chicago
Downtown Chicago
9.2/10 Wonderful! (1,144 reviews)
Oct 4 - Oct 7
3 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,183, price is now $817 per person
$817
per person
found 1 day ago
Overall, it was really really nice
Reviewed on Aug 1, 2026
3.5-star property
The Chicago Hotel Collection - Wrigleyville
Lakeview
7/10 Good! (1,008 reviews)
Oct 17 - Oct 24
7 night stay
Fort Lauderdale (FLL) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Fort Lauderdale (FLL)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,795, price is now $1,251 per person
$1,251
per person
found 9 hours ago
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
$145 nightly
The price is $172 total per night
$172 total
Aug 30 - Aug 31
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
$152 nightly
The price is $181 total per night
$181 total
Aug 17 - Aug 18
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
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
$206 nightly
The price is $242 total per night
$242 total
Aug 29 - Aug 30
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 luggage storage, securing valuables, and concierge services. Additional amenities include a conference center, a business center, and a computer station.
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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