Chicago Heights Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Nice room and view. Rooftop was gorgeous

Reviewed on Jul. 13, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Nice property, very walkable. Front desk was great. Bar area nice & welcome drink nice. Concierge was not around. Got suite with 2 full baths which was awesome with teens. Great stay overall!

Reviewed on Jul. 12, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Amazing customer service

Reviewed on Jul. 13, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I love Virgin air and expected a 5-star experience. Hotel checkin was not all that welcoming, but efficientl. They had no valet service and basically told us we were on our own. Thought ok I need a drink so went to the rooftop bar. An afterthought at this hotel. Cushions were dirty and faded. Barely staffed. More like a rooftop bar in costs rica than downtown Chicago. Room was nice and stylish. The highlight of the stay tbh as was the coffee shop.

Reviewed on Jul. 13, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Superb customer service, clean hotel!

Reviewed on Jun. 13, 2025

Ready to book your vacation to Chicago Heights?

 

Choose your dates

Chicago Heights Hotel Deals

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
The price is CA $86 per night from Jul 21 to Jul 22
CA $86
CA $97 total
Jul 21 - Jul 22
includes taxes & fees
6.8/10 (1,180 reviews)
"Staffs were very polite, respectful and helpful"

Reviewed on Jul. 9, 2025

Motel 6 Bridgeview, IL
Hilton Chicago/Oak Lawn
Hilton Chicago/Oak Lawn
3.5 out of 5
9333 S Cicero Ave, Oak Lawn, IL
The price is CA $174 per night from Aug 5 to Aug 6
CA $174
CA $200 total
Aug 5 - Aug 6
includes taxes & fees
8/10 Very Good! (1,008 reviews)
"The property was very clean the staff was very respectful overall I had a great experience here"

Reviewed on Jul. 12, 2025

Hilton Chicago/Oak Lawn
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 $135 per night from Jul 28 to Jul 29
CA $135
CA $159 total
Jul 28 - Jul 29
includes taxes & fees
7.6/10 Good! (1,532 reviews)
"Just a quick down evening…headed home…good sleep"

Reviewed on Jul. 10, 2025

Sleep Inn Midway Airport Bedford Park
See all 740 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 $615 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.

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