Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
4.0-star property
Level Chicago Fulton Market
Downtown Chicago
9.2/10 Wonderful! (561 reviews)
Oct 21 - Oct 25
4 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 $1,492, price is now $886 per person
$886
per person
found 1 day ago
4.5-star property
Swissotel - Chicago
Downtown Chicago
9/10 Wonderful! (3,512 reviews)
Oct 21 - Oct 25
4 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 $1,647, price is now $965 per person
$965
per person
found 1 day ago
Every staff member we encountered were wonderful and welcoming. Great location. Stayed four nights and would definitely stay again.
Reviewed on Sep 12, 2026
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (5,174 reviews)
Oct 21 - Oct 25
4 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 $1,759, price is now $1,035 per person
$1,035
per person
found 1 day ago
4.0-star property
Level Chicago – Old Town
Downtown Chicago
9.2/10 Wonderful! (520 reviews)
Oct 21 - Oct 25
4 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 $1,591, price is now $1,001 per person
$1,001
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 25
4 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 $1,502, price is now $972 per person
$972
per person
found 1 day ago
Confusing layout on the pier, front desk upon check in should have explained the layout better. Did not appreciate the forced $29 daily fee for the ferris wheel tickets, $10 restaurant credit and water. It really should be optional. Without it, I would have eaten at the hotel abd drank the crap bottle water. Really bad pillows and cannot close the curtains. Not in my friend's room either.
Reviewed on Sep 12, 2026
Top rated hotels for your Chicago vacation package
River Hotel
75 East Wacker Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.5 mi from city center
$127 nightly
The price is $151 total per night
$151 total
Sep 13 - Sep 14
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
1.74 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
0.43 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
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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