Book Exclusive Gary Vacation Packages

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Gary flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Freehand Chicago

Freehand Chicago

4 out of 5
Downtown Chicago
Price was CA $1,288, price is now CA $884 per person
CA $884
per person
Oct 4 - Oct 9
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $2,032, price is now CA $1,405 per person
CA $1,405
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was CA $1,494, price is now CA $1,075 per person
CA $1,075
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park 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 $1,990, price is now CA $1,450 per person
CA $1,450
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,556, price is now CA $1,144 per person
CA $1,144
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Top Gary hotels deals

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 $199 per night
CA $199
CA $237 total
Aug 30 - Aug 31
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 Grant Park and Millennium Park are located nearby.
Free WiFi
Restaurant
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $166 per night
CA $166
CA $197 total
Aug 31 - Sep 1
includes taxes & fees
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Free WiFi
Restaurant
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 $392 per night
CA $392
CA $507 total
Aug 14 - Aug 15
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 Grant Park and Millennium Park are located nearby.
Pool
Hot tub
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $261 per night
CA $261
CA $351 total
Sep 1 - Sep 2
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Soldier Field and Grant Park are located nearby.
Free WiFi
Restaurant
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 $201 per night
CA $201
CA $239 total
Aug 30 - Aug 31
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 Grant Park and Soldier Field are located nearby.
Free WiFi
Restaurant
HI Chicago Hostel

HI Chicago Hostel

1.5 out of 5
24 E Ida B Wells Drive Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $150 per night
CA $150
CA $176 total
Aug 31 - Sep 1
includes taxes & fees
Stay at this hostel in Chicago. Enjoy free WiFi, a 24-hour front desk, and 2 meeting rooms. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Free WiFi
Restaurant
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See all available properties in Gary
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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.

Stay near popular Gary attractions

A beach with a red house on a small island, surrounded by trees and rocky shoreline.

Marquette Beach

9.4/10 (3 reviews)
Why not spend a lazy afternoon at Marquette Beach during your trip to Miller Beach?
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Frequently asked questions

How much are vacation packages to Gary?
With deals starting as low as CA $884, 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

A pier extending into calm waters at sunset with a clear sky.
A historic building with a tower, adjacent modern buildings, and a parking lot.
A cityscape with historic buildings, including a large brick structure with arched windows and a white building with a grid pattern.
An aerial view of a cityscape with industrial buildings, a large church, and residential areas.
A beach with waves and a sunset.