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.
4.0-star property
Chicago Marriott Downtown Magnificent Mile
Downtown Chicago
8.8/10 Excellent! (1,010 reviews)
Oct 21 - Oct 24
3 night stay
Boston (BOS) to Chicago (ORD)
Frontier Airlines • Non-stop • Coach
Chicago (ORD) to Boston (BOS)
American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $932, price is now $638 per person
$638
per person
found 1 day ago
4.5-star property
Swissotel - Chicago
Downtown Chicago
9/10 Wonderful! (3,512 reviews)
Oct 21 - Oct 24
3 night stay
Boston (BOS) to Chicago (ORD)
Frontier Airlines • Non-stop • Coach
Chicago (ORD) to Boston (BOS)
American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,428, price is now $869 per person
$869
per person
found 1 day ago
Lovely room
Reviewed on Sep 15, 2026
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (5,174 reviews)
Oct 21 - Oct 24
3 night stay
Boston (BOS) to Chicago (ORD)
Frontier Airlines • Non-stop • Coach
Chicago (ORD) to Boston (BOS)
American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,384, price is now $879 per person
$879
per person
found 1 day ago
4.0-star property
Level Chicago – Old Town
Downtown Chicago
9.2/10 Wonderful! (520 reviews)
Nov 11 - Nov 15
4 night stay
Boston (BOS) to Chicago (ORD)
Delta • Coach
Chicago (ORD) to Boston (BOS)
JetBlue Airways • Coach
Save 100% on your flight
Price was $1,184, price is now $764 per person
$764
per person
found 1 day ago
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (2,681 reviews)
Oct 21 - Oct 24
3 night stay
Boston (BOS) to Chicago (ORD)
Frontier Airlines • Non-stop • Coach
Chicago (ORD) to Boston (BOS)
American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,349, price is now $897 per person
$897
per person
found 1 day ago
We were so excited about spending the time at Sable hotel however, when we arrived, it was the House of horrors. It was very filthy. Went to go grab an extra blanket and a butt plug fell out of it. Asked for them to please come clean the room they said housekeeping was not there and would take care of it tomorrow so we spent the first night in a filthy dirty room as they had no extra room rooms due to multiple concerts being held that weekend. My advice the location is great, but there’s other options that are more affordable.
Reviewed on Sep 14, 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 27 - Sep 28
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
$161 nightly
The price is $191 total per night
$191 total
Sep 28 - Sep 29
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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