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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,359, price is now CA $957 per person
CA $957
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (2,683 reviews)
Place is in a great location but once you go past the lobby its very dated. Small rooms and had lots of trouble getting in touch with the front desk when we needed something.
Reviewed on May 7, 2026
Swissotel - Chicago
Downtown Chicago
Price was CA $1,447, price is now CA $962 per person
CA $962
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Having stayed in the lovely Swissotel Bosphorus/Istanbul, I was hesitant to compare Swissotel experience & hope Chicago would be as good. No. Not even close.
The elevated Swissotel brand is not represented here well in this building at all. The valet is $87! Self park is $70 and the self park area doesn’t even have an elevator up to the lobby, you have to walk through a dark, confusing, and claustrophobic garage to stairs then to elevator. Staff were tactful & kind, it’s just the building is old, needs renovation, & the room air is stuffy. A positive bright light was the stunning view from the gym and the lobby ambience & smell.
Reviewed on May 6, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,683, price is now CA $1,142 per person
CA $1,142
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
My stay was exceptional the staff were very polite and patient, they answered all my questions. I had a very nice view will definitely book again
Reviewed on May 6, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,626, price is now CA $1,148 per person
CA $1,148
per person
Jun 30 - Jul 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,144 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!
Reviewed on May 5, 2026
Gary Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $182 per night from May 12 to May 13
CA $182
CA $216 total
May 12 - May 13
includes taxes & fees
8/10 Very Good! (10,186 reviews)
The hotel looks really cool as it’s really old. The rooms are very basic, a coffee maker and a tiny tv. The south tower is right on the train line so it can be noisy with the train rattling past. The staff was nice. We didn’t use many of the amenities (like restaurants) so I can’t comment on them. ...
Reviewed on May 8, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from May 25 to May 26
CA $217
CA $298 total
May 25 - May 26
includes taxes & fees
8.6/10 Excellent! (2,780 reviews)
I’ve stayed at the Hilton Chicago many times, and I keep going back because it is always a great experience. The staff is great, making check in easy and using the amenities easy. The property is clean and well maintained, so it feels luxurious, and it’s right downtown in the loop so you have easy ...
Reviewed on May 6, 2026
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $231 per night from May 22 to May 23
CA $231
CA $307 total
May 22 - May 23
includes taxes & fees
9.2/10 Wonderful! (1,070 reviews)
Really nice and super clean
Reviewed on May 6, 2026
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.
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
