Book Exclusive Gary Vacation Packages
Gary flight + hotel packages
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was CA $805, price is now CA $552 per person
CA $552
per person
Jan 14 - Jan 17
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Westin Michigan Avenue Chicago
Downtown Chicago
Price was CA $1,805, price is now CA $819 per person
CA $819
per person
Dec 27 - Dec 31
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), 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.
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,874, price is now CA $1,183 per person
CA $1,183
per person
Dec 26 - Jan 2
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Stay at this 4-star 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
Downtown Chicago
Price was CA $1,188, price is now CA $806 per person
CA $806
per person
Jan 14 - Jan 17
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 5-star 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,009, price is now CA $701 per person
CA $701
per person
Jan 14 - Jan 17
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 4-star 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.
Top Gary hotels deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $289 per night
CA $289
CA $339 total
Nov 6 - Nov 7
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. 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
720 S Michigan Ave, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $159 per night
CA $159
CA $228 total
Nov 24 - Nov 25
includes taxes & fees
Stay at this 4-star 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
Travelodge by Wyndham Downtown Chicago
65 E Harrison St, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $125 per night
CA $125
CA $147 total
Nov 17 - Nov 18
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 Garden Inn Chicago Downtown South Loop
55 E 11th Street, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $130 per night
CA $130
CA $152 total
Nov 24 - Nov 25
includes taxes & fees
Stay at this 3-star 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 Grant Park and Soldier Field are located nearby.
Pool
Pet-friendly
Homewood Suites by Hilton Chicago Downtown South Loop
59 E. 11th Street, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $177 per night
CA $177
CA $208 total
Nov 11 - Nov 12
includes taxes & fees
Stay at this 3-star 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 Grant Park and Soldier Field are located nearby.
Pool
Breakfast included
Best Western Grant Park Hotel
1100 S Michigan Ave, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $118 per night
CA $118
CA $138 total
Nov 10 - Nov 11
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
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
Explore the great outdoors at Marquette Park, a lovely green space in Miller Beach. While you're in the area, stroll along the lakeside.
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.
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.
Frequently asked questions
Photos of local treasures
Browse Gary vacation photos for more inspiration
