Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (4,770 reviews)
Aug 29 - Aug 31
2 night stay
Dallas (DAL) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Price was $820, price is now $591 per person
$591
per person
found 1 day ago
Very pleasant stay and cleanliness
Reviewed on Jul 29, 2026
3.0-star property
Holiday Inn Chicago North-Evanston by IHG
Downtown Evanston
8.6/10 Excellent! (2,028 reviews)
Oct 13 - Oct 19
6 night stay
Dallas (DFW) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Dallas (DFW)
Frontier Airlines • Coach
Save 100% on your flight
Price was $941, price is now $670 per person
$670
per person
found 11 hours ago
4.5-star property
Pendry Chicago
Downtown Chicago
9.2/10 Wonderful! (1,144 reviews)
Sep 3 - Sep 6
3 night stay
Dallas (DAL) to Chicago (ORD)
Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,281, price is now $922 per person
$922
per person
found 4 hours ago
The property is one of the coolest places in Chicago. Conveniently located to the Magnificent Mile, Millennial Park, and the Theater District.
Reviewed on Jul 28, 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
$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 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 10 - Aug 11
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
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 CityPASS®: Experience 5 must-see attractions
$144
per adult
94% of travellers recommend
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