Chicago Heights Vacations from $688

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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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,085, price is now $688 per person
$688
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great and helpful staff very clean, a place where you don’t feel out of place

Reviewed on Apr 25, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $2,032, price is now $1,025 per person
$1,025
per person
Jun 9 - Jun 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,914 reviews)
Great location, breakfast with many options and clean rooms.

Reviewed on Apr 26, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,323, price is now $765 per person
$765
per person
Jun 9 - Jun 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,636 reviews)
Great location and value

Reviewed on Apr 25, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,616, price is now $1,588 per person
$1,588
per person
Jun 9 - Jun 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,280 reviews)
Really good spot and location. Staff was super helpful and nice.

Reviewed on Apr 22, 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,199, price is now $1,391 per person
$1,391
per person
Jun 9 - Jun 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,348 reviews)
Conveniently located, cute bars and restaurants nearby and within walking distance of a tour bus stop. The room was clean, comfortable beds and the staff was pleasant.

Reviewed on Apr 22, 2026

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Chicago Heights Hotel Deals

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
$110 nightly
The price is $129 total per night from May 25 to May 26
$129 total
May 25 - May 26
Total with taxes and fees
8/10 Very Good! (1,844 reviews)
The stay itself was average, but there was an uncomfortable incident during checkout where a guest was yelling and loudly complaining about the checkout time. Security had to be called, and the front desk agent even threatened to involve the police. The situation made the atmosphere feel tense and, ...

Reviewed on Apr 25, 2026

Sleep Inn Midway Airport Bedford Park
DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
5000 W 127th St Alsip IL
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $139 total per night from May 10 to May 11
$139 total
May 10 - May 11
Total with taxes and fees
8.4/10 Very Good! (1,021 reviews)
Yes, I felt safe walking to and from my car. The room was very comfortable and clean. I didn't have the breakfast, I've heard its good.

Reviewed on Apr 26, 2026

DoubleTree by Hilton Chicago - Alsip
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
$126 nightly
The price is $145 total per night from May 3 to May 4
$145 total
May 3 - May 4
Total with taxes and fees
8.4/10 Very Good! (1,311 reviews)
Fff

Reviewed on Apr 26, 2026

Hilton Chicago/Oak Lawn
See all 849 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 $688 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.