Chicago Heights Vacations from $196

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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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was $460, price is now $196 per person
$196
per person
Feb 4 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18/10 Exceptional! (1,001 reviews)
Great location and restaurant

Reviewed on Nov 19, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was $508, price is now $220 per person
$220
per person
Feb 4 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.4/10 Exceptional! (317 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.

Reviewed on Oct 28, 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,177, price is now $516 per person
$516
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
17.6/10 Exceptional! (1,075 reviews)
Great location and staff was very accommodating. Rooms were on the small side.

Reviewed on Nov 19, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $521, price is now $251 per person
$251
per person
Feb 4 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.8/10 Exceptional! (1,130 reviews)
The room had no soundproofing. Every night a car was revving loudly across Michigan Ave around midnight, making it impossible to sleep without noise-cancelling AirPods.

Reviewed on Nov 18, 2025

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $443, price is now $226 per person
$226
per person
Feb 4 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.4/10 Exceptional! (48 reviews)
The room seemed under furnished. Only one chair with a table.

Reviewed on Nov 5, 2025

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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
$130 nightly
The price is $150 total per night from Nov 30 to Dec 1
$150 total
Nov 30 - Dec 1
Total with taxes and fees
8.2/10 Very Good! (1,125 reviews)
It was convenient to the location I had to be at - it would have been nice to have a microwave in the room

Reviewed on Nov 13, 2025

Hilton Chicago/Oak Lawn
Hyatt Place Chicago Midway Airport

Hyatt Place Chicago Midway Airport

3 out of 5
6550 S Cicero Ave Chicago IL
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $149 total per night from Nov 23 to Nov 24
$149 total
Nov 23 - Nov 24
Total with taxes and fees
9/10 Wonderful! (1,175 reviews)
Clean Room and staff was very professional .

Reviewed on Nov 14, 2025

Hyatt Place Chicago Midway Airport
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
$38 nightly
The price is $43 total per night from Nov 23 to Nov 24
$43 total
Nov 23 - Nov 24
Total with taxes and fees
7/10 Good! (1,283 reviews)
Michael at the front desk was very attentive and responded to my questions with confidence. The room was clean and smelled clean unlike the previous stay a couple years ago. Jon well done in bringing it to a better star review.

Reviewed on Nov 9, 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.

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 $196 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.