Chicago Vacation Packages
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Top Chicago vacation package deals
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Holiday Inn Chicago North-Evanston by IHG
Downtown Evanston
8.6/10 Excellent! (1,818 reviews)
Jun 16 - Jun 22
6 night stay
New York (JFK) to Chicago (ORD)
Delta • Roundtrip • Coach
Save 100% on your flight
Price was $1,014, price is now $714 per person
$714
per person
found 23 hours ago
Nice rooms, employees and breakfast was good
Reviewed on Feb 13, 2026
4.0-star property
Eurostars Magnificent Mile
Downtown Chicago
9/10 Wonderful! (3,314 reviews)
May 27 - May 30
3 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
Spirit Airlines • Coach
Save 100% on your flight
Price was $1,075, price is now $723 per person
$723
per person
found 1 day ago
In convenient area either by walking or uber
Reviewed on Oct 18, 2025
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (2,401 reviews)
May 27 - May 30
3 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
Spirit Airlines • Coach
Save 100% on your flight
Price was $1,651, price is now $1,157 per person
$1,157
per person
found 1 day ago
Courteous staff, clean room, conveniently located right on the pier.
Reviewed on Nov 3, 2025
4.0-star property
Embassy Suites by Hilton Chicago O'Hare Rosemont
8.8/10 Excellent! (1,283 reviews)
Jun 18 - Jun 25
7 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
Spirit Airlines • Coach
Save 100% on your flight
Price was $1,143, price is now $801 per person
$801
per person
found 1 day ago
We enjoyed our stay. Clean room, professional staff and great proximity to O’Hare.
Reviewed on Mar 3, 2026
4.0-star property
Graduate by Hilton Evanston
Downtown Evanston
9/10 Wonderful! (1,001 reviews)
Jun 16 - Jun 22
6 night stay
New York (JFK) to Chicago (ORD)
Delta • Roundtrip • Coach
Save 100% on your flight
Price was $1,455, price is now $1,024 per person
$1,024
per person
found 23 hours ago
We really like it here - it's a bit quirky, but it's very comfortable and the staff are great.
Reviewed on May 28, 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
$110 nightly
The price is $129 total per night
$129 total
Apr 5 - Apr 6
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.
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Free Cancellation
Reserve now, pay when you stay
1.35 mi from city center
$119 nightly
The price is $140 total per night
$140 total
Apr 12 - Apr 13
Total with taxes and fees
At Hilton Chicago/Magnificent Mile Suites, guests enjoy features like an indoor pool, a gym, and free WiFi in public areas. Valet parking is available for USD 82 per night. The front desk has multilingual staff on hand 24/7 to help with dry cleaning/laundry, securing valuables, and luggage storage. Additional amenities include conference space, a business center, and express check-out.
Pool
Pet friendly
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.83 mi from city center
$135 nightly
The price is $159 total per night
$159 total
Apr 12 - Apr 13
Total with taxes and fees
Guests of Embassy Suites by Hilton Chicago Downtown River North have access to an indoor pool, a gym, and WiFi in public areas. Valet parking is available for USD 79.00 per night. Multilingual staff at the front desk are standing by 24/7 to help with dry cleaning/laundry, concierge services, and luggage storage. Additional amenities include meeting rooms, conference space, and a business center.
Pool
Breakfast included
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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