Gary Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*
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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
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination
Kimpton Gray Hotel by IHG
Park Hyatt Chicago
The Peninsula Chicago

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 $162 per night from Nov 23 to Nov 24
CA $162
CA $193 total
Nov 23 - Nov 24
includes taxes & fees
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 $151 per night from Nov 27 to Nov 28
CA $151
CA $220 total
Nov 27 - Nov 28
includes taxes & fees
8.6/10 Excellent! (3,526 reviews)
"The main area of the hotel is old and beautiful. The rooms are quite basic and due for upgrades. The bathroom had stool on the toilet when we arrived. No fan in the bathroom or working window so the room got very humid when we showered. I’m surprised that I didn’t see mold. Bed was comfy."

Reviewed on Nov 5, 2026

Hilton Chicago
Sentral Michigan Avenue

Sentral Michigan Avenue

4 out of 5
808 SOUTH MICHIGAN AVENUE Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $178 per night from Dec 7 to Dec 8
CA $178
CA $209 total
Dec 7 - Dec 8
includes taxes & fees
9/10 Wonderful! (1,404 reviews)
"Nice place, Clean, floor to ceiling window had a great view of the city."

Reviewed on Nov 5, 2026

Sentral Michigan Avenue
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.

Stay near popular Gary attractions

Frequently asked questions

How much does a Gary vacation package cost?
You'll find cheap prices from CA $1,190 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.