Chicago Heights Vacations from $386

Book a Hotel + Flight or Car together to unlock savings

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 Emily Hotel

The Emily Hotel

Downtown Chicago
Save 100% on your flight
$386
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,347 reviews)
This is a great hotel

Reviewed on Oct 21, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
$894
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Great place to stay in Chicago!

Reviewed on Oct 21, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$775
per person
Nov 28 - Dec 1
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
Save 100% on your flight
$1,183
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
Always an incredible hotel! Definitely one of the best in the USA

Reviewed on Oct 21, 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
Save 100% on your flight
$577
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
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Chicago Heights Hotel Deals

Star Inn & Suites

Star Inn & Suites

460 W Lincoln Hwy Chicago Heights IL
Fully refundableReserve now, pay when you stay
$99 nightly
$111 total
Oct 26 - Oct 27
Total with taxes and fees
Star Inn & Suites
Sleep Inn Midway Airport Bedford Park

Sleep Inn Midway Airport Bedford Park

6650 S Cicero Ave Chicago IL
Fully refundable
$101 nightly
$119 total
Nov 12 - Nov 13
Total with taxes and fees
Sleep Inn Midway Airport Bedford Park
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

4900 S Lake Shore Dr Chicago IL
$148 nightly
$174 total
Nov 17 - Nov 18
Total with taxes and fees
7/10 Good! (1,012 reviews)
"For $247.00 I expected better accommodations… I chose the hotel because of its close proximity to a venue I attended and the distance to the venue was a plus. Problems: the online pictures are deceptive. The hotel looks great through all the filters. The reality is that the hotel, although as clean ..."

Reviewed on Oct 22, 2026

Chicago Lake Shore Hotel
See all 869 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 $386 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.