Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
2.0-star property
Travelodge by Wyndham Downtown Chicago
Downtown Chicago
7.6/10 Good! (2,711 reviews)
Oct 22 - Oct 25
3 night stay
Boston (BOS) to Chicago (ORD)
United • Roundtrip • Coach
Price was $666, price is now $448 per person
$448
per person
found 1 day ago
It’s a 100 year old hotel that has been minimally updated, so it certainly doesn’t look fancy but it is adequate. Bed was comfortable. Sheets were basic, no pills. Window AC loud but works. Microwave and fridge in room. Cable tv. Bathtub/shower old tile and stained but clean. Towels clean and thick. No pool. WiFi seemed fine. Best thing is great location close to park, museums, restaurants, and L stop. No fills but worked for what we needed.
Reviewed on Aug 17, 2026
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (4,907 reviews)
Oct 22 - Oct 25
3 night stay
Boston (BOS) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $1,292, price is now $841 per person
$841
per person
found 1 day ago
I had an amazing time at the hotel. The employees were helpful and the rooftop view is amazing.
Reviewed on Aug 17, 2026
4.5-star property
Swissotel - Chicago
Downtown Chicago
9/10 Wonderful! (3,537 reviews)
Sep 24 - Sep 28
4 night stay
Boston (BOS) to Chicago (ORD)
Frontier Airlines • Non-stop • Coach
Chicago (ORD) to Boston (BOS)
JetBlue Airways • Non-stop • Coach
Save 100% on your flight
Price was $1,430, price is now $944 per person
$944
per person
found 1 day ago
4.0-star property
Level Chicago Fulton Market
Downtown Chicago
9.2/10 Wonderful! (544 reviews)
Oct 4 - Oct 9
5 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • Non-stop • Coach
Chicago (ORD) to Boston (BOS)
Delta • Non-stop • Coach
Save 100% on your flight
Price was $1,665, price is now $1,113 per person
$1,113
per person
found 1 day ago
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.
Reviewed on Aug 12, 2026
4.5-star property
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (3,808 reviews)
Sep 24 - Sep 28
4 night stay
Boston (BOS) to Chicago (ORD)
Frontier Airlines • Non-stop • Coach
Chicago (ORD) to Boston (BOS)
JetBlue Airways • Non-stop • Coach
Save 100% on your flight
Price was $1,356, price is now $955 per person
$955
per person
found 1 day ago
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
$115 nightly
The price is $136 total per night
$136 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 dry cleaning/laundry. 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
$143 nightly
The price is $170 total per night
$170 total
Aug 30 - Aug 31
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 wedding services.
Pet friendly
Free WiFi
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Free Cancellation
Reserve now, pay when you stay
15.67 mi from city center
$238 nightly
The price is $279 total per night
$279 total
Sep 12 - Sep 13
Total with taxes and fees
Guests of Hilton Chicago O'Hare Airport enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is USD 77 per day if you plan to drive, or hop aboard the free airport shuttle (available on request). Multilingual staff at the front desk are standing by 24/7 to help with concierge services, securing valuables, and luggage storage. Additional amenities include a conference center, a business center, and a computer station.
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: 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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