Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
4.0-star property
The Blackstone, Autograph Collection
Downtown Chicago
9/10 Wonderful! (1,003 reviews)
Jan 16 - Jan 23
7 night stay
Atlanta (ATL) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Atlanta (ATL)
Frontier Airlines • Coach
Save 100% on your flight
Price was $705, price is now $370 per person
$370
per person
found 1 day ago
Elegant, old-fashioned (in a good way) with modern touches. Very quiet, well appointed.
Reviewed on Nov 18, 2023
4.5-star property
The Westin Michigan Avenue Chicago
Downtown Chicago
8.8/10 Excellent! (1,070 reviews)
Dec 27 - Dec 31
4 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Price was $1,184, price is now $491 per person
$491
per person
found 1 day ago
Everything is EXCELLENT. But don’t consider the hotel for breakfast lunch or dinner
Reviewed on Oct 18, 2025
4.5-star property
Pendry Chicago
Downtown Chicago
9.4/10 Exceptional! (1,110 reviews)
Jan 16 - Jan 23
7 night stay
Atlanta (ATL) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Atlanta (ATL)
Frontier Airlines • Coach
Price was $1,015, price is now $479 per person
$479
per person
found 1 day ago
Pendry was historic and great
Reviewed on Jul 5, 2024
4.5-star property
theWit Chicago, a Hilton Hotel
Downtown Chicago
9/10 Wonderful! (1,011 reviews)
Jan 16 - Jan 23
7 night stay
Atlanta (ATL) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Atlanta (ATL)
Frontier Airlines • Coach
Save 100% on your flight
Price was $721, price is now $372 per person
$372
per person
found 1 day ago
It's really a problem that the elevators are prioritized for people going to the rooftop vs guests of the hotel. We had to wait as several elevators took people to the rooftop while guests were standing there waiting on an elevator. Really disappointing.
Reviewed on Aug 4, 2025
4.0-star property
The Emily Hotel
Downtown Chicago
9.2/10 Wonderful! (1,248 reviews)
Jan 16 - Jan 23
7 night stay
Atlanta (ATL) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Atlanta (ATL)
Frontier Airlines • Coach
Price was $1,053, price is now $546 per person
$546
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
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
$108 nightly
The price is $127 total per night
$127 total
Dec 8 - Dec 9
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 securing valuables, dry cleaning/laundry, and concierge services. Additional amenities include meeting rooms, conference space, and a business center.
Pool
Breakfast included
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.43 mi from city center
$102 nightly
The price is $120 total per night
$120 total
Nov 13 - Nov 14
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 securing valuables, concierge services, and dry cleaning/laundry. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
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
$101 nightly
The price is $119 total per night
$119 total
Dec 7 - Dec 8
Total with taxes and fees
Guests of Hilton Chicago/Magnificent Mile Suites enjoy a gym, free WiFi in public areas, and conference space. Valet parking is available for USD 82 per night. The front desk has multilingual staff on hand 24/7 to help with concierge services, luggage storage, and dry cleaning/laundry. Additional amenities include a business center, express check-out, and an ATM.
Pet friendly
Free WiFi
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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