Chicago Vacation Packages
Book a Stay + Flight or Car to save on your trip
Top Chicago vacation package deals
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (2,790 reviews)
Mar 5 - Mar 8
3 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $630, price is now $394 per person
$394
per person
found 1 day ago
Enjoyed our stay in Chicago...coldest weekend ever, but the accommodations were tip-top. Room was clean and well appointed. Staff was incredibly attentive and responsive. The breakfast buffet was very good and a great value for this well located hotel.
Reviewed on Dec 15, 2025
4.0-star property
The Emily Hotel
Downtown Chicago
9.2/10 Wonderful! (1,264 reviews)
Mar 4 - Mar 8
4 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $820, price is now $466 per person
$466
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
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.4/10 Exceptional! (1,773 reviews)
Mar 5 - Mar 8
3 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,031, price is now $630 per person
$630
per person
found 1 day ago
Food was amazing and the staff was amazing. Room was incredible! Felt like we were royalty on our visit!
Reviewed on Oct 13, 2025
4.0-star property
Level Chicago – Old Town
Downtown Chicago
9/10 Wonderful! (380 reviews)
Mar 5 - Mar 8
3 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $648, price is now $411 per person
$411
per person
found 1 day ago
We always love staying here. Such great service and nice accommodations.
Reviewed on Nov 20, 2025
4.5-star property
Pendry Chicago
Downtown Chicago
9.4/10 Exceptional! (1,130 reviews)
Mar 5 - Mar 8
3 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $647, price is now $416 per person
$416
per person
found 1 day ago
Pendry was historic and great
Reviewed on Jul 5, 2024
Top rated hotels for your Chicago vacation package
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
$89 nightly
The price is $105 total per night
$105 total
Jan 5 - Jan 6, 2026
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 securing valuables, luggage storage, and dry cleaning/laundry. Additional amenities include a business center, express check-out, and a porter/bellhop.
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.05 mi from city center
$156 nightly
The price is $179 total per night
$179 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
Guests of Palmer House a Hilton Hotel enjoy a full-service spa, an indoor pool, and a 24-hour gym. Parking is available for USD 57 per night (USD 85 per night for valet parking), and there's also limo/town car service. Multilingual staff at the front desk are standing by 24/7 to help with securing valuables, concierge services, and access to locker space. Other amenities at this luxury hotel include a conference center, a business center, and express check-in.
Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.5 mi from city center
$88 nightly
The price is $103 total per night
$103 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
At Club Quarters Hotel Wacker at Michigan, Chicago, guests have access to a gym, free WiFi in public areas, and meeting rooms. Valet parking is offered for USD 76 per day. The 24-hour front desk has staff standing by to help with luggage storage, dry cleaning/laundry, 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 a business center, coffee/tea in a common area, and a computer station.
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.
Explore More Ways to Travel with Travelocity
- Cabin Rentals in Monroe Station
- Villas in Monroe Station
- Magnificent Mile Hotels
- Hotels near Grant Park
- Hotels near Chicago Riverwalk
- Condo Rentals in Jackson Station
- Motels in Jackson Station
- Hotels near Richard J. Daley Center
- Hotels near Navy Pier
- Hotels near DePaul University-Loop Campus
- Hotels near McCormick Place
- 2 Star Hotels in Theatre District
- 5 Star Hotels in Theatre District
- Arcade Hotels in Theatre District
- Business Hotels in Theatre District
- Hotels with Suites in Theatre District
- Hotels with Airport Transfers in Theatre District
- Hotels with Air Conditioning in Theatre District
- Hotels with Childcare in Theatre District
- Luxury Hotels in Theatre District
- Hotels on the River in Theatre District
- Winery Hotels in Theatre District
- Theatre District Hotels
- Hotels near House of Blues Chicago
- Cheap Hotels in The Loop
- Hotels with WiFi in The Loop
- Hotels with Free Parking in The Loop
- Hotels with an Indoor Pool in The Loop
- Romantic Getaways & Hotels in The Loop
- Hotels with Shopping in The Loop
- Hotels with a Wedding Venue in The Loop
- The Loop Hotels
- Hotels near Chicago City Hall
- Hotels near State Street
- Hotels near Roosevelt University
- Hotels near Kluczynski Building
- Hotels near Chagall's Four Seasons
- Hotels near Chicago Cultural Center
- Hotels near Millennium Park
- Apartments in Jackson Station
- Extended Stay Hotels in Jackson Station
- Inns in Jackson Station
- Hotels near Chicago Loop Synagogue
- Hotels near Chicago Union Station
- Condo Rentals in Madison-Wabash Station
- Hostels in Madison-Wabash Station
- Resorts in Madison-Wabash Station
- Hotels near Michigan Avenue
- Hotels near Art Institute of Chicago
- Hotels near Chicago Theatre
- Hotels near Willis Tower
- Hotels near United Center
- Apartments in Monroe Station
- B&B in Monroe Station
- Apartments in Adams-Wabash Station
- Hostels in Adams-Wabash Station
- Inns in Adams-Wabash Station
- Motels in Adams-Wabash Station
- Resorts in Adams-Wabash Station
- Hotels near Daley Plaza
- Hotels with Pool in Downtown Chicago
- Hotels with Balconies in Downtown Chicago
- Hotels with Free Breakfast in Downtown Chicago
- Hotels with Free Parking in Downtown Chicago
- Luxury Hotels in Downtown Chicago
- Downtown Chicago Hotels
- Hotels near Soldier Field
- St. Stanislaus Kostka Church
- Magnificent Mile Vacations
- Cooper Dual Language Academy
- Grant Park
- Chicago Riverwalk
- Goose Island Vacations
- Navy Pier
- Museum of Broadcast Communications
- Mccormick Place
- Wicker Park Vacations
- Chicago Children's Museum
- Water Tower Place
- American Medical Association Headquarters
- Ping Tom Memorial Park
- Wrigley Field
- Chicago Loop Synagogue
- Buckingham Fountain
- Museum of Contemporary Art Chicago
- Illinois Institute of Technology
- Art Institute of Chicago
- Harris Theater
- Chicago Theatre
- Chicago Museum Campus Vacations
- Willis Tower
- Holy Innocents Church
- United Center
- Marina City
- Peggy Notebaert Nature Museum
- Lincoln Hall
- Downtown Chicago Vacations
- Hotels in Magnificent Mile
- Hotels near Art Institute of Chicago
- Visit Navy Pier
- Hotels near Michigan Avenue
- Cheap Hotels in Downtown Chicago
- Hotels near Chicago Theatre
- Luxury Hotels in Downtown Chicago
- Hotels near Millennium Park
- Hotels with Suites in Downtown Chicago
- Visit Art Institute of Chicago
- Chicago vacations
- Hotels near Chicago Riverwalk
- Hotels in Central Chicago
- Hotels in River North
- Hotels in Downtown Chicago
- Hotels near Navy Pier
- Hotels near Soldier Field
- Hotels near Chicago Union Station
- Hotels near Grant Park
- Hotels in The Loop
