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.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
per person
Oct 17 - Oct 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,418 reviews)
Hotel felt hot. initially air conditoner wasn't working but was fixed. Still didn't feel like it got very cold in the room. Bathtub was very slippery.

Reviewed on Aug. 7, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Loved the attention to details that made the experience exceptional.

Reviewed on Aug. 6, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Everything was great

Reviewed on Aug. 9, 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
Transport access walking distance to take train to midway airport was easy and convenient

Reviewed on Aug. 7, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,063 reviews)
It is located on Navy Pier which was very convenient for us. The view was wonderful of the skyline and harbor. The room was very nice and had a refrigerator,,but lacked a microwave. The room and restaurant were quite expensive for what they were, but I guess we were paying for the location.

Reviewed on Aug. 9, 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 $185 per night from Sep 1 to Sep 2
CA $185
CA $217 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (8,926 reviews)
"Took water awhile to get hot for shower, and parking is ridiculously expensive. Other than that enjoyed staying at hotel"

Reviewed on Aug. 8, 2025

Congress Plaza Hotel
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 $193 per night from Sep 2 to Sep 3
CA $193
CA $266 total
Sep 2 - Sep 3
includes taxes & fees
8.4/10 Very Good! (2,050 reviews)
"Amazing. Family friendly. The staff were so good"

Reviewed on Aug. 7, 2025

Hilton Chicago
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 $130 per night from Aug 25 to Aug 26
CA $130
CA $153 total
Aug 25 - Aug 26
includes taxes & fees
7.2/10 Good! (2,269 reviews)
Stay for Lollalapoolza
"Absolutely amazing stay. I travel A LOT and this staff was the best hotel staff I have ever had (including mutli 5 star properties). Thank you for being a part of our great weekend."

Reviewed on Aug. 5, 2025

Travelodge by Wyndham Downtown Chicago
See all 1,669 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 $839 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.