Gary Vacation Packages

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Your Gary Vacation

From its rich history to its cultural experiences and beyond, there's loads to love about Gary. Discover the wonders of this interesting city with a Gary vacation package that's customized for you. Hard Rock Casino Northern Indiana, Ameristar Casino East Chicago and Indiana University Northwest are just some of the many sights worth visiting during your trip to Gary. A few quick clicks is all it takes to build the perfect Gary vacation on Expedia.

Top Gary Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Delta Hotels by Marriott Chicago Willowbrook

Delta Hotels by Marriott Chicago Willowbrook

3 out of 5
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.2/10 Very Good! (429 reviews)
The staff was very friendly. Fast check-in and check-out with no issues! Second time staying here and will stay again!

Reviewed on Jul. 24, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Nice hotel with a great breakfast buffet

Reviewed on Jul. 25, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Large rooms, excellent view and location

Reviewed on Jul. 24, 2025

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,584 reviews)
This is our 2nd time staying here and it is wonderful. Very nice staff, close to everything. Highly recommend!

Reviewed on Jul. 24, 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
The staff were very friendly and had great food and activity recommendations. Facility was clean. Walking distance to downtown, Navy Pier, Millennium Park. Highly recommend this hotel.

Reviewed on Jul. 25, 2025

Ready to book your vacation to Gary?

 

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Gary Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $183 per night from Aug 24 to Aug 25
CA $183
CA $215 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (8,964 reviews)
"The staff was very friendly and helpful"

Reviewed on Jul. 25, 2025

Congress Plaza Hotel
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Aug 25 to Aug 26
CA $147
CA $173 total
Aug 25 - Aug 26
includes taxes & fees
7/10 Good! (2,256 reviews)
"Everything was great"

Reviewed on Jul. 21, 2025

Travelodge by Wyndham Downtown Chicago
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $272 per night from Jul 26 to Jul 27
CA $272
CA $359 total
Jul 26 - Jul 27
includes taxes & fees
8.4/10 Very Good! (2,010 reviews)
"First time staying here. The staff were great and the hotel has a lot going on. The bed in my room was so comfortable for my short stay. Would stay again. Nice people work here and the security officers were pleasant as well. ."

Reviewed on Jul. 19, 2025

Hilton Chicago
See all 1,612 properties in Gary
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

Discover the most popular places to visit in Gary

Majestic Star Casino

Why not try your luck with a visit to Majestic Star Casino during your visit to Gary? While you're in the area, find time to visit its casinos.

Majestic Star Casino

Frequently asked questions

How much does a Gary vacation package cost?
You'll find cheap prices from CA $620 on Expedia for your Gary break. However, a range of factors like the season, choice of hotel and length of stay will determine how much your vacation to Gary costs.
What are the cheapest months to go to Gary?
To pick up cheap Gary vacation packages, organize your getaway outside of peak periods like public holidays and major events. You'll generally find better availability and lower prices when it's less busy.
How many days is enough for Gary?
Typically, a handful of days is enough for a Gary vacation. With a well-planned itinerary, you can see all the top sights including Lake Street Beach, as well as discover some hidden treasures along the way.
How to find the best Gary package deals?
Start your search for a Gary package deal by entering your travel dates and destination under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Gary package deal right away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Gary escape off to a flying start.
Is it cheaper to book a Gary vacation as a package?
You can enjoy significant savings on your Gary escape by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to view some great hotel prices and airfares. 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 Gary?
Secure fantastic discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Gary getaway.
How to plan a trip to Gary?

  1. Choose when to go: Check your schedule and pack your bags. Your preferred season and the type of activities on offer will also help you decide when to escape to Gary.
  2. Figure out your budget: Ensure you have enough money to pay for everything from food and transportation to experiences and flights. Your accommodations will likely be the largest expense during your trip to Gary.
  3. Decide how long to go away for: Now that you're more familiar with Gary, you can figure out the right length of your break. Put together a draft plan and allocate enough time to get through everything on your must-do list.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to pick a Gary vacation package that brings all your bookings together.

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