Chicago Vacation Packages
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Top Chicago vacation package deals
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
8.2/10 Very Good! (2,365 reviews)
May 1 - May 4
3 night stay
Boston (BOS) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $669, price is now $418 per person
$418
per person
found 1 day ago
The rooms were clean and smelled fresh.
Reviewed on Jan 8, 2026
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (2,790 reviews)
May 1 - May 4
3 night stay
Boston (BOS) to Chicago (ORD)
United • Roundtrip • Coach
Price was $1,227, price is now $527 per person
$527
per person
found 1 day ago
I recommend 100% Everything was good, the staff, room and the food. Also, it is located in a good area.
Reviewed on Jan 14, 2026
4.0-star property
La Banque Hotel
9.4/10 Exceptional! (447 reviews)
May 2 - May 7
5 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $835, price is now $474 per person
$474
per person
found 15 hours ago
Beautiful boutique hotel with great staff!
Reviewed on Sep 16, 2022
4.0-star property
Eurostars Magnificent Mile
Downtown Chicago
8.8/10 Excellent! (3,098 reviews)
May 1 - May 4
3 night stay
Boston (BOS) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $791, price is now $511 per person
$511
per person
found 1 day ago
In convenient area either by walking or uber
Reviewed on Oct 18, 2025
4.0-star property
The Emily Hotel
Downtown Chicago
9.2/10 Wonderful! (1,264 reviews)
May 1 - May 4
3 night stay
Boston (BOS) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $822, price is now $532 per person
$532
per person
found 1 day ago
Cute and trendy hotwl but there was a loud party on-site which ruined experience. It felt clean but our mini fridge had takeout left from former guest, so maid service obviously missed that.
Reviewed on Jul 26, 2025
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
$93 nightly
The price is $109 total per night
$109 total
Feb 22 - Feb 23
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 dry cleaning/laundry, concierge services, and securing valuables. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.91 mi from city center
$123 nightly
The price is $144 total per night
$144 total
Mar 4 - Mar 5
Total with taxes and fees
A 24-hour gym and free WiFi in public areas are features at Hotel Riu Plaza Chicago. Multilingual staff at the 24-hour front desk can assist with luggage storage, concierge services, and dry cleaning/laundry.
Breakfast included
Free WiFi
Hilton Chicago
720 S Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.6 mi from city center
$164 nightly
The price is $192 total per night
$192 total
Feb 27 - Feb 28
Total with taxes and fees
Guests staying at Hilton Chicago enjoy an indoor pool, a gym, and a sauna. Valet parking is offered for USD 88.00 per day. The 24-hour front desk has multilingual staff ready to assist with luggage storage, securing valuables, and dry cleaning/laundry. Other amenities at this historic hotel include free WiFi in public areas, a hot tub, and a conference center.
Pool
Hot Tub
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.
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