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.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was CA $1,069, price is now CA $664 per person
CA $664
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Everyone there was friendly and gave us a lot of places to go eat for our one year anniversary

Reviewed on Aug. 21, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $3,954, price is now CA $2,330 per person
CA $2,330
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug. 10, 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,354, price is now CA $817 per person
CA $817
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
One of the tvs didnt work, and neither did the room phone. Dislike the texting communication, and having to go thru 3rd party just to call front desk.

Reviewed on Aug. 17, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,851, price is now CA $1,121 per person
CA $1,121
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on Aug. 19, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,902, price is now CA $1,211 per person
CA $1,211
per person
Oct 22 - Oct 25
found 21 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (335 reviews)
Great except parking

Reviewed on Aug. 19, 2025

Ready to book your vacation to Gary?

 

Choose your dates

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 $165 per night from Aug 24 to Aug 25
CA $165
CA $194 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (9,023 reviews)
"“Self park” to outsiders or people from out of country means something else. Please publish that you have NO parking available. Parking lots around the Hotel are not specifically designated for guests. Plus the high rate of daily cost will drain your vacation budget if it was not accounted for."

Reviewed on Aug. 20, 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 $194 per night from Sep 2 to Sep 3
CA $194
CA $269 total
Sep 2 - Sep 3
includes taxes & fees
8.4/10 Very Good! (2,093 reviews)
"Very updated"

Reviewed on Aug. 19, 2025

Hilton Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL
The price is CA $161 per night from Sep 2 to Sep 3
CA $161
CA $189 total
Sep 2 - Sep 3
includes taxes & fees
7.2/10 Good! (2,294 reviews)
"The room was adequate for me no fridge or microwave but I didn't need them, but the bed was comfy slept like a baby. Staff was excellent rooms were clean I have no complaints"

Reviewed on Aug. 19, 2025

Travelodge by Wyndham Downtown Chicago
See all 1,679 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 $664 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.