Chicago Heights Vacations from $255

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Your Chicago Heights Vacation

When you book a vacation package to Chicago Heights, you can relax and enjoy your escape knowing your travel plans are in order. Discover the many gems of this vibrant city while staying in a neighborhood like Glenwood, which is great for golfing. There's plenty to put on your itinerary during a trip to Chicago Heights, beginning with popular attractions such as Coyote Run Golf Course and Ravisloe Country Club. No matter your travel plans or the size of your budget, putting together the ultimate tailored Chicago Heights vacation is simple with Expedia.

The Latest Chicago Heights vacation packages

Price found within the past 48 hours. Click for updated prices.
The French Country Inn Lake Geneva

The French Country Inn Lake Geneva

3 out of 5
Save 100% on your flight
Price was $437, price is now $255 per person
$255
per person
Nov 14 - Nov 16
just found
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (146 reviews)
Popular with drunks that party way past reasonable quiet hours.

Reviewed on Sep 27, 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,560, price is now $638 per person
$638
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,046 reviews)
One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done.

Reviewed on Oct 2, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,098, price is now $543 per person
$543
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
First time in Chicago, the hotel was walkable to a lot of things. Loved the location. Was clean and felt comfortable.

Reviewed on Oct 5, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,180, price is now $613 per person
$613
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
This hotel was very nice however they have one elevator that was working for 36 floors. We constantly had to wait for the elevator and sometimes we waited so long that we decided to take the stairs and walk down 14 flights, we ended up doing this 3 times. This was incredibly inconvenient! When the elevator was working, it stopped on every single floor as we went down. We were there from Wednesday to Sunday, it was very frustrating!

Reviewed on Oct 5, 2025

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,206, price is now $654 per person
$654
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
Front desk clerk was great. Made us feel like VIPs.

Reviewed on Oct 5, 2025

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Chicago Heights Hotel Deals

Hampton Inn by Hilton Chicago-Midway Airport

Hampton Inn by Hilton Chicago-Midway Airport

2.5 out of 5
6540 S Cicero Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $176 total per night from Nov 2 to Nov 3
$176 total
Nov 2 - Nov 3
Total with taxes and fees
8.4/10 Very Good! (1,236 reviews)
"Great airport shuttle service very knowledgeable and helpful driver. Nice receptionist allowed us to check in our bags early which was much appreciated. The rooms were spotlessly clean and comfortable."

Reviewed on Oct 3, 2025

Hampton Inn by Hilton Chicago-Midway Airport
Hilton Chicago/Oak Lawn

Hilton Chicago/Oak Lawn

3.5 out of 5
9333 S Cicero Ave, Oak Lawn, IL
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $142 total per night from Oct 13 to Oct 14
$142 total
Oct 13 - Oct 14
Total with taxes and fees
8.2/10 Very Good! (1,041 reviews)
"From the moment I entered the building, the smell alone was Stellar. The rooms and service were as expected per online photographs, the fitness center was great, it not huge but enoughselectionto get a good workout, the hallways were clean and quiet. There a a small breakfast spot across from the ..."

Reviewed on Sep 30, 2025

Hilton Chicago/Oak Lawn
Motel 6 Bridgeview, IL

Motel 6 Bridgeview, IL

2 out of 5
9625 S 76th Ave, Bridgeview, IL
Fully refundableReserve now, pay when you stay
$52 nightly
The price is $58 total per night from Nov 3 to Nov 4
$58 total
Nov 3 - Nov 4
Total with taxes and fees
6.8/10 (1,254 reviews)
"I love everything about it Quiet Great Vending machines"

Reviewed on Sep 26, 2025

Motel 6 Bridgeview, IL
See all 798 properties in Chicago Heights
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.

Chicago Heights Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Midway Intl. Airport (MDW)
Population
30,300
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Odyssey Fun World, Midwest Carvers Museum and William W. Powers State Recreation Area

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Frequently asked questions

How much does a Chicago Heights vacation package cost?
Offering excellent value package deals from $255 on Expedia, you'll be surprised at how little a vacation to Chicago Heights costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Chicago Heights?
December, January and February are the best times to search for cheap Chicago Heights vacation packages. Choosing to travel in quieter periods means you can typically find reduced prices on flights and hotels.
How many days is enough for Chicago Heights?
Generally, a handful of days is enough to check out the major attractions during your Chicago Heights vacation. However, if you'd like to have more time to relax or take day trips, think about extending your itinerary.
How to find the best Chicago Heights package deals?
Begin your search for a Chicago Heights package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Chicago Heights package deal straight away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Chicago Heights adventure underway.
Is it cheaper to book a Chicago Heights vacation as a package?
You can enjoy significant savings on your next Chicago Heights retreat by booking a personalized vacation package. Check the "Package" heading, then enter your travel dates and destination to browse some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Chicago Heights?
If you're planning an impromptu Chicago Heights adventure, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score amazing deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Chicago Heights vacation packages?
Your Chicago Heights getaway is meant to be a relaxing escape from your busy life, not a reason for money-related stress. So to allow you more flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.