Chicago Heights Vacations from $400

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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.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $599, price is now $400 per person
$400
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,357 reviews)
Fantastic hotel in a great central location with helpful staff - what more could we ask for?!

Reviewed on Apr 11, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $694, price is now $415 per person
$415
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
The breakfast was delicious. A great stay in downtown Chicago.

Reviewed on Apr 12, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $836, price is now $502 per person
$502
per person
Jun 12 - Jun 15
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
It was too cold for the pool! The property is in a great location, the staff kind and very helpful. The on site restaurant is quite wonderful. I would have to say we had the best meal of our stay of 4 nights in Chicago!the rooms are large and airy and very clran

Reviewed on Apr 7, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,551, price is now $953 per person
$953
per person
Jun 16 - Jun 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
We love staying at the Sable. Easy in and out parking. The Valet staff is wonderful. We enjoyed our breakfast. The room and view is always amazing.

Reviewed on Apr 11, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,157, price is now $725 per person
$725
per person
Jun 16 - Jun 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Great location! Easy parking and the rooms were gorgeous! We will definitely stay here next time we visit Chicago

Reviewed on Apr 10, 2026

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Chicago Heights Hotel Deals

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
$122 nightly
The price is $140 total per night from Apr 19 to Apr 20
$140 total
Apr 19 - Apr 20
Total with taxes and fees
8.4/10 Very Good! (1,278 reviews)
Clean room staff was great

Reviewed on Apr 11, 2026

Hilton Chicago/Oak Lawn
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
7353 S Cicero Avenue Chicago IL
Fully refundable
$135 nightly
The price is $157 total per night from May 10 to May 11
$157 total
May 10 - May 11
Total with taxes and fees
8.4/10 Very Good! (1,002 reviews)
The property had just recently completed a complete renovation. The lobby, rooms, bar/restaurant were immaculate, well-furnished and well maintained. Some sections of the exterior were still being renovated (pool area). The American flag flying in front of the facility was beyond repair and should ...

Reviewed on Apr 9, 2026

Holiday Inn Chicago – Midway Airport S by IHG
Sleep Inn Midway Airport Bedford Park

Sleep Inn Midway Airport Bedford Park

2.5 out of 5
6650 S Cicero Ave Chicago IL
Fully refundable
$107 nightly
The price is $126 total per night from Apr 19 to Apr 20
$126 total
Apr 19 - Apr 20
Total with taxes and fees
8/10 Very Good! (1,829 reviews)
Very nice and clean but back paying for parking was a huge surprise

Reviewed on Apr 12, 2026

Sleep Inn Midway Airport Bedford Park
See all 852 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.

Find the Best Chicago Heights Vacation Packages

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 $400 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.

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