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.
2.0-star property
Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts
5.4/10 (1,000 reviews)
Sep 2 - Sep 4
2 night stay
Austin (AUS) to Chicago (ORD)
United • Roundtrip • Coach
Price was $414, price is now $240 per person
$240
per person
found 8 hours ago
Air conditioning not working
Toilet leaking, told clerk at front desk, he told us: put a towel over the water
Tv not working ( turn on and off by itself)
No fridge, I asked for an iron, to borrow or I could rented, he told they didn’t have any.
Terrible, not recommended.
Reviewed on Jul 6, 2026
2.0-star property
Super 8 by Wyndham Morton Grove/Chicago
6.8/10 (1,001 reviews)
Sep 2 - Sep 4
2 night stay
Austin (AUS) to Chicago (ORD)
United • Roundtrip • Coach
Price was $443, price is now $259 per person
$259
per person
found 8 hours ago
It was very nice. I liked the outdoor patio. There used ti be a pool there when I stayed a long time ago!
Reviewed on Jul 7, 2026
2.0-star property
Motel 6 Palatine, IL - Chicago Northwest
6.8/10 (600 reviews)
Sep 2 - Sep 4
2 night stay
Austin (AUS) to Chicago (ORD)
United • Roundtrip • Coach
Price was $445, price is now $260 per person
$260
per person
found 8 hours ago
My room was very clean and the carpeting in the halls looked new. It is very basic, but I was comfortable, had no complaints, and slept well.
Reviewed on Jul 6, 2026
4.0-star property
Level Chicago - River North
Downtown Chicago
9.2/10 Wonderful! (1,020 reviews)
Sep 12 - Sep 20
8 night stay
Austin (AUS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Austin (AUS)
Frontier Airlines • Coach
Save 100% on your flight
Price was $3,065, price is now $1,812 per person
$1,812
per person
found 11 hours ago
There is a family lounge and pool and it was really helpful for us. (we have 2 kids bc7&4 yo)
The spacious room with full kitchen is very comfortable as well.
We have 2 negative points. One is location. It is located around River North but a little bit far from the busy area. So there are not so many places to eat around. Another one is the water pressure in the shower is very weak.
Reviewed on Jul 7, 2026
Top rated hotels for your Chicago vacation package
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.98 mi from city center
$197 nightly
The price is $234 total per night
$234 total
Jul 9 - Jul 10
Total with taxes and fees
Guests of Omni Chicago Hotel have access to a 24-hour gym, in-room fitness, and free WiFi in public areas. Valet parking is offered for USD 89.49 per night. The 24-hour front desk has staff standing by to help with concierge services, dry cleaning/laundry, and securing valuables. Other amenities at this luxury hotel include conference space, express check-out, and a porter/bellhop.
Pet friendly
Free WiFi
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
$163 nightly
The price is $193 total per night
$193 total
Jul 27 - Jul 28
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 a banquet hall.
Pet friendly
Free WiFi
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.43 mi from city center
$185 nightly
The price is $220 total per night
$220 total
Jul 9 - Jul 10
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.
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 CityPASS®: Experience 5 must-see attractions
$144
per adult
94% of travellers recommend
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
