Central Chicago Vacation Packages
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Top Central Chicago vacation package deals
Price found within the past 48 hours. Click for updated prices.
4.5-star property
The Talbott, Autograph Collection
Downtown Chicago
9.4/10 Exceptional! (165 reviews)
Dec 2 - Dec 5
3 night stay
Austin (AUS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Austin (AUS)
American Airlines • Coach
Save 100% on your flight
Price was $736, price is now $470 per person
$470
per person
found 1 day ago
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.6/10 Exceptional! (1,995 reviews)
Nov 26 - Nov 30
4 night stay
Austin (AUS) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,643, price is now $959 per person
$959
per person
found 23 hours ago
4.0-star property
Renaissance Chicago Downtown Hotel
Downtown Chicago
9.2/10 Wonderful! (1,004 reviews)
Oct 22 - Oct 25
3 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Boston (BOS)
American Airlines • Coach
Save 100% on your flight
Price was $1,438, price is now $899 per person
$899
per person
found 1 day ago
4.5-star property
The Wade
Downtown Chicago
8.6/10 Excellent! (2,042 reviews)
Dec 2 - Dec 5
3 night stay
Austin (AUS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Austin (AUS)
American Airlines • Coach
Save 100% on your flight
Price was $760, price is now $489 per person
$489
per person
found 1 day ago
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (5,174 reviews)
Dec 2 - Dec 5
3 night stay
Austin (AUS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Austin (AUS)
American Airlines • Coach
Save 100% on your flight
Price was $833, price is now $536 per person
$536
per person
found 1 day ago
Great location. So much to do in walking distance and hotel was great.
Reviewed on Sep 16, 2026
Top rated hotels for your Central Chicago vacation package
River Hotel
75 East Wacker Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.42 mi from city center
$159 nightly
The price is $190 total per night
$190 total
Sep 20 - Sep 21
Total with taxes and fees
River Hotel features a gym, free WiFi in public areas, and meeting rooms. Valet parking is available for USD 76 per night. The front desk is staffed 24/7 to help with luggage storage, securing valuables, and concierge services. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include conference space, a business center, and express check-in.
Pet friendly
Free WiFi
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Free Cancellation
Reserve now, pay when you stay
1.67 mi from city center
$179 nightly
The price is $213 total per night
$213 total
Oct 13 - Oct 14
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
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.48 mi from city center
$164 nightly
The price is $195 total per night
$195 total
Sep 27 - Sep 28
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
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View all propertiesLowest 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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