Chicago Vacation Packages
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Top Chicago vacation package deals
Price found within the past 48 hours. Click for updated prices.
3.5-star property
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
8.4/10 Very Good! (3,932 reviews)
Nov 3 - Nov 10
7 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $972, price is now $567 per person
$567
per person
found 1 day ago
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.6/10 Exceptional! (2,003 reviews)
Nov 3 - Nov 10
7 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,952, price is now $1,672 per person
$1,672
per person
found 1 day ago
4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
8.2/10 Very Good! (2,960 reviews)
Nov 3 - Nov 10
7 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,097, price is now $632 per person
$632
per person
found 1 day ago
.
Reviewed on Sep 1, 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
$95 nightly
The price is $113 total per night
$113 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 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
$114 nightly
The price is $135 total per night
$135 total
Sep 7 - Sep 8
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 82 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 fireplace in the lobby.
Pet friendly
Free WiFi
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
1 mi from city center
Guests staying at Kasa Magnificent Mile Chicago enjoy a gym, free WiFi in public areas, and a convenience store. Self parking is available for USD 51.00 per day. Front-desk staff can help with luggage storage, and provide local restaurant recommendations.
Kitchen
Washer
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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