Chicago Heights Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Chicago Heights Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
$458
per person
Oct 26 - Oct 30
found 23 hours ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The pictures match the rooms. The hotel staff was polite and pleasant and very helpful.
Reviewed on Aug 23, 2026
Level Chicago Fulton Market
Downtown Chicago
$731
per person
Oct 26 - Oct 30
found 23 hours ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Great staff and amenities. Beautiful pool, bbq area and more. Terrific room
Only issues was parking was $68 a day, plus incidental holds of $200 per day. Security is strong and is close to Fulton Market and we would walk over to the RiverWalk every day
As the hotel is permanent residents and renters security is job 1. Problems you have to go to the third floor to get a baggage cart and you have to leave your drivers license, which I didn’t care for and to get into the garage you have to call security and more than once no one answered and you had to go into the building and find them.
For the money your room key or a key pad should allow you in.
Reviewed on Aug 21, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
$654
per person
Oct 26 - Oct 30
found 23 hours ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago – Old Town
Downtown Chicago
$627
per person
Oct 26 - Oct 30
found 23 hours ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
$494
per person
Oct 26 - Oct 30
found 23 hours ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Perfect location. Staff was friendly & accommodating.
Reviewed on Aug 23, 2026
River Hotel
Downtown Chicago
$462
per person
Oct 26 - Oct 30
found 23 hours ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
To be honest, we only used the hotel facilities for the basics; the staff was always attentive, and the hotel was in excellent condition. However, the standout feature is its prime location—right in the heart of downtown Chicago—with great connections to all the major tourist attractions to walking distance.
Reviewed on Aug 23, 2026
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See all available trips from Columbus to Chicago Heights
View all tripsChicago Heights Vacation Packages
Trying to figure out a way to bundle your flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® Chicago Heights vacation packages can help. We're here to book everything you'll need to make your Chicago Heights trip one to remember. Our Travel Center is a one-stop shop where you can put together the best vacation package for you. AARP Travel Center has an incredible selection of flights and hotels, and local activities to choose from.
Chicago Heights Hotel Deals
You can choose from around 800 hotels. Whether you want to stay in the heart of the city or pick a spot that is near all the Chicago Heights hot spots, we have plenty of options available.
We have competitive rates on everything from luxury hotels that satisfy all the vacation must-haves to inexpensive hotels which are great for those on a budget. You can browse our vast catalog of options and pick the hotel that is perfect for you and your family. With AARP Travel Center's Chicago Heights hotel packages, you not only get a great rate on your flight, but also a wonderful place to stay.
Things to do in Chicago Heights
Chicago Heights has about 30,284 people that call this city their home. If you needed a break from the bustle of a big city, then you picked the right town. With Chicago Heights's growing artistic community and a rich past that is a beacon for history aficionados you may have a hard time fitting everything into one trip.
If you are looking for more, then head over to our "Things to Do" page for more inspiration or to book an activity in Chicago Heights.
Package Your Chicago Heights Vacation and Save
With so much to see and do in Chicago Heights, you'll be wanting to focus on your itinerary, not spending time to finding the cheapest hotel. AARP Travel Center allows you to quickly get everything you wish for, and save some cash on your vacation. You can coordinate your entire vacation, including activities in Chicago Heights from only one place. The hardest packing you'll have to do is for your suitcase. Bundle today and save!
Top Hotel Deals
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the overall value in our reviews. ...
Sleep Inn Midway Airport Bedford Park
6650 S Cicero Ave Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
Quality Inn & Suites Orland Park - Chicago
8800 W 159th St Orland Park IL
Book a stay at this business-friendly hotel in Orland Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Motel 6 - Chicago, IL
10022 South Halsted Street Chicago IL
Stay at this motel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Abbott Park and Martin Luther King Drive are located ...
Motel 6 Bridgeview, IL
9625 S 76th Ave Bridgeview IL
Stay at this motel in Bridgeview. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
DoubleTree by Hilton Chicago - Alsip
5000 W 127th St Alsip IL
Book a stay at this business-friendly hotel in Alsip. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Wind Creek Southland Casino and Hotel
17300 S Halsted St Hazel Crest IL
Book a stay at this luxury resort in Hazel Crest. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Ravisloe Country Club and Oak Hill ...
Baymont by Wyndham Chicago/Alsip
12801 South Cicero Alsip IL
Book a stay at this business-friendly hotel in Alsip. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Hyatt Place Chicago Midway Airport
6550 S Cicero Ave Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Courtyard by Marriott Chicago Midway Airport
6610 S Cicero Ave Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
6500 S Cicero Ave Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
Ameristar Casino Hotel East Chicago
777 Ameristar Blvd. East Chicago IN
Book a stay at this beach hotel in East Chicago. Enjoy free parking, 5 restaurants, and a marina. Our guests praise the helpful staff and the clean rooms in ...
Super 8 by Wyndham South Holland
17225 Halsted St South Holland IL
Book a stay at this business-friendly hotel in South Holland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Days Inn and Suites by Wyndham Hammond, IN
4000 Calumet Avenue Hammond IN
Book a stay at this business-friendly hotel in Hammond. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff in our ...
Don't see what you're looking for?
See all available properties in Chicago Heights
View all propertiesLowest 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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Thu, Oct 15 - Mon, Oct 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$148
Roundtrip
found 14 hours ago
Thu, Oct 15 - Mon, Oct 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$173
Roundtrip
found 14 hours ago
Thu, Oct 15 - Mon, Oct 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$183
Roundtrip
found 14 hours ago
Thu, Oct 1 - Sun, Oct 4
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197
Roundtrip
just found
Tue, Sep 29 - Tue, Oct 6
LAX
Los Angeles Intl.
MDW
Midway Intl.
$197
Roundtrip
found 1 day ago
Best points of interest in Chicago Heights
- Lake Michigan Vacations
- Indiana Dunes National Park Vacations
- University of Chicago Vacations
- Griffin Museum of Science and Industry Vacations
- Credit Union 1 Amphitheatre Vacations
- SeatGeek Stadium Vacations
- Hard Rock Casino Northern Indiana Vacations
- State Street Vacations
- Tinley Park Convention Center Vacations
- President Obama’s Chicago Family Home Vacations
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