Book Exclusive Gary Vacation Packages

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Gary flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was CA $1,103, price is now CA $718 per person
CA $718
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,815, price is now CA $1,131 per person
CA $1,131
per person
Mar 6 - Mar 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,956, price is now CA $1,265 per person
CA $1,265
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,088, price is now CA $721 per person
CA $721
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,311, price is now CA $881 per person
CA $881
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Top Gary hotels deals

Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $157 per night
CA $157
CA $224 total
Dec 30 - Dec 31
includes taxes & fees
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Soldier Field are located nearby.
Pool
Hot tub
Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

3 out of 5
59 E. 11th Street Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $111 per night
CA $111
CA $130 total
Jan 5 - Jan 6, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Soldier Field and Millennium Park are located nearby.
Pool
Breakfast included
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $283 per night
CA $283
CA $333 total
Dec 31 - Jan 1, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Free WiFi
Restaurant
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
55 E 11th Street Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $100 per night
CA $100
CA $117 total
Jan 5 - Jan 6, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Soldier Field and Millennium Park are located nearby.
Pool
Pet-friendly
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
1100 S Michigan Ave Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $99 per night
CA $99
CA $116 total
Jan 5 - Jan 6, 2026
includes taxes & fees
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Soldier Field and Millennium Park are located nearby.
Free WiFi
Restaurant
Sentral Michigan Avenue

Sentral Michigan Avenue

4 out of 5
808 SOUTH MICHIGAN AVENUE Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $162 per night
CA $162
CA $230 total
Jan 4 - Jan 5, 2026
includes taxes & fees
Book a stay at this business-friendly aparthotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Soldier Field and Millennium Park are located nearby.
Pool
Kitchen
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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.

Popular places to visit

Marquette Park

Marquette Park

Explore the great outdoors at Marquette Park, a lovely green space in Miller Beach. While you're in the area, stroll along the lakeside.

Marquette Park

Hard Rock Casino Northern Indiana

Why not try your luck with a visit to Hard Rock Casino Northern Indiana during your visit to Gary? While in the area, you can find time to visit its casinos.

Hard Rock Casino Northern Indiana

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 are vacation packages to Gary?
With deals starting as low as CA $718, flight and hotel packages are a superb way to stretch your travel budget. Gary, here you come!
How long should my Gary vacation be?
If you need some guidance, most travelers spend around 2 nights vacationing in Gary. But to uncover the true essence of this place, stay a few extra days. That way you can see more and really soak up the local culture.
Where can I get the best vacation package deals for Gary?
With as many as 400 air carriers and 1,000,000 properties across the globe, you can't go wrong with Travelocity. Scroll through our impressive range and create the perfect package deal to Gary. Isn't it great when organizing a trip is that easy?
Why should I purchase my Gary vacation bundle with Travelocity?
We take the hassle out of travel planning. Whether you're seeking an amazing new place to discover or want to ensure you get the best price on offer, we've got your back. Our 24/7 customer support, high-quality service and Price Match Guarantee mean you can book with confidence with Travelocity.
Can I save money on my Gary car rental if I combine it with a hotel or flight?
Combining your flight, hotel and car into a Gary vacation package is an excellent way to score the best deal. Plus, having your own wheels gives you freedom to get to all those big-name sights you're itching to explore. Located 97 kilometers from Gary, Six Flags Great America is one place that should have a place on your itinerary. Load up the car and make a day trip of it.
Which airport is best for Gary?
It's highly likely you'll be landing at O'Hare Intl. Airport (ORD), located 64 kilometers northwest of downtown Gary. Midway Intl. Airport (MDW) (40 kilometers away from central Gary) and South Bend Intl. Airport (SBN) (88 kilometers away from central Gary) are your other options.
What is there to do in Gary?
While taking the path less traveled is rewarding, you shouldn't miss the popular sights that make a place famous. Hard Rock Casino Northern Indiana and Indiana University Northwest are a couple of them in Gary.
Where should I stay when visiting Gary?
If you're searching for someplace comfortable to lay your head, have a look at the Modern Boho Beach House with Hot Tub. It's the top choice for many visitors.

Photos of local treasures

Browse Gary vacation photos for more inspiration

Photo by Lawrence Tellez
Photo by Lawrence Tellez
Photo by Louis Ploth
Photo by Louis Ploth