Chicago Heights Vacation Packages

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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.

Top Chicago Heights Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $2,153, price is now CA $1,484 per person
CA $1,484
per person
Sep 20 - Sep 23
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,136 reviews)
Mediocre all around and for the price point not worth it. Great location. But nothing else compelling. Food was only ok. Service was only ok. Nothing memorable. Will seek somewhere else next time.

Reviewed on Jul 8, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Price was CA $3,926, price is now CA $2,363 per person
CA $2,363
per person
Sep 20 - Sep 23
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
I liked everything except that the air conditioner in the hotel hallway was too cold

Reviewed on Jul 8, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $7,380, price is now CA $4,994 per person
CA $4,994
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Front desk staff was super helpful and enthusiastic. Smooth check-in, and checkout.

Reviewed on Jul 8, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,290, price is now CA $1,614 per person
CA $1,614
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Wonderful amenities, clean and great location. The only thing I did not care for was checking myself in. Front staff welcome you but you have to complete your own check in. After a long day if travel the last thing a person wants to do is complete forms. Lowers the Luxury feel of the property when the front desk does not do what an average Holiday Inn does.

Reviewed on Jul 6, 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
Price was CA $3,176, price is now CA $2,335 per person
CA $2,335
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
View was beautiful, accommodations were excellent.

Reviewed on Jul 8, 2026

Ready to book your vacation to Chicago Heights?

 

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Chicago Heights Hotel Deals

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 refundableReserve now, pay when you stay
The price is CA $161 per night from Jul 15 to Jul 16
CA $161
CA $203 total
Jul 15 - Jul 16
includes taxes & fees
8.2/10 Very good! (1,024 reviews)
"Don’t like Parking fee."

Reviewed on Jul 7, 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 refundableReserve now, pay when you stay
The price is CA $167 per night from Jul 13 to Jul 14
CA $167
CA $197 total
Jul 13 - Jul 14
includes taxes & fees
8/10 Very good! (1,974 reviews)
"room was small"

Reviewed on Jul 7, 2026

Sleep Inn Midway Airport Bedford Park
Motel 6 - Chicago, IL

Motel 6 - Chicago, IL

2 out of 5
10022 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Aug 3 to Aug 4
CA $122
CA $144 total
Aug 3 - Aug 4
includes taxes & fees
7.4/10 Good! (394 reviews)
"This was a solo backpack trip for me so I don’t mind the hotel - there was no elevator working, the floors/ ground leading to the door of the rooms were dirty and unstable as in not smooth- I personally don’t mind marijuana smoke but if you are sensitive to it you may have a problem - I will say ..."

Reviewed on Jul 8, 2026

Motel 6 - Chicago, IL
See all 816 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Chicago Heights vacation package cost?
You'll find cheap prices from CA $1,484 on Expedia for your Chicago Heights escape. However, a range of factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Chicago Heights costs.
What are the cheapest months to go to Chicago Heights?
If you're looking to snag a cheap Chicago Heights vacation package, consider planning a trip in January, February and November. You'll typically find better prices on accommodations and flights during these quieter months — ideal for budget-conscious travellers.
How many days is enough for Chicago Heights?
Typically, a handful of days is enough to visit the main sights during your Chicago Heights vacation. However, if you want to have time to unwind or take day trips, think about extending your trip.
How to find the best Chicago Heights package deals?
Use Expedia's filter tool to help you find some great Chicago Heights package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Chicago Heights package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Chicago Heights vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging hotels and flights individually. Better still, you can tailor your Chicago Heights getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Chicago Heights?
If you're considering a spur-of-the-moment Chicago Heights adventure, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can land amazing deals on your flights and hotels by booking well in advance.
How to plan a trip to Chicago Heights?

  1. Choose your travel dates: What you plan to do in Chicago Heights and your favourite season can help you decide when to get away.
  2. Plan your budget wisely: In addition to the price of your hotel, you should factor in other expenses. These include food, flights and transportation. Also, put aside some extra funds for unexpected expenses that may arise during your trip to Chicago Heights.
  3. Decide how long to go away for: Now that you know more about Chicago Heights, you can work out the right length of your vacation. Create a rough plan and allocate enough time to cover everything you want to see.
  4. Bundle your airfare and accommodations: After you've settled on your dates and duration, book the perfect Chicago Heights vacation package for you.

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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.