Grand Boulevard Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
Plan, book, travel with confidence
Better together
Save up to CA $775 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top Holiday Package Deals in Grand Boulevard
Price found within the past 48 hours. Click for updated prices.
The Westin Michigan Avenue Chicago
Downtown Chicago
per person
Aug. 10 - Aug. 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,004 reviews)
Perfect area to go shopping, check out tourist attractions, or relax at the beach. Very convenient area to head to Lakefront Trail as well for a morning run. Staff was helpful and friendly during every interaction. I really loved all the benefits you received through the destination fee. Property was clean and attentive. In a very walkable area and close to public transportation.
Reviewed on Jun. 3, 2024
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug. 10 - Aug. 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,212 reviews)
Very nice staff except for the guy at the front desk with the hair braided back very rude. I pray I never encounter him again I come to the Trump all the time and this was my first encounter with him very unwelcoming and dry.
Reviewed on Jun. 4, 2024
Chicago Marriott Downtown Magnificent Mile
Downtown Chicago
Save 100% on your flight
per person
Aug. 10 - Aug. 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,006 reviews)
my stay went really well! staff were friendly and always attentive. housekeeping were really friendly and nice. everything met our needs and the view was nice to see. thank you!
Reviewed on Jun. 2, 2024
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
per person
Jul. 16 - Jul. 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.8/10 Excellent! (208 reviews)
This is not a full service hotel. This is a long term stay or furnished apartment. Great sauna and gym.
Reviewed on Jun. 3, 2024
Where to stay in Grand Boulevard
Find the best Grand Boulevard areas and neighborhoods for the activities you enjoy most. Learn more about Grand Boulevard
Downtown Chicago
4 out of top 10 points of interest in this area
Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Millennium Park are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
Grand Boulevard Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $225 per night from Jun. 16 to Jun. 17
CA $225
CA $264 total
includes taxes & fees
Jun 16 - Jun 17
7.6/10 Good! (6,830 reviews)
"I like the location."
Reviewed on Jun. 2, 2024
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $276 per night from Jul. 2 to Jul. 3
CA $276
CA $324 total
includes taxes & fees
Jul 2 - Jul 3
8/10 Very Good! (2,353 reviews)
Perfect location for a Chicago stay with family
"We have stayed here several times and have had a great experience each time. The staff is always friendly, especially the Bellman, and everyone else we encountered. The room was clean and comfortable. The breakfast was delicious as always. We choose this hotel for its location specifically. We can ..."
Reviewed on Jun. 4, 2024
River Hotel
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from Jun. 30 to Jul. 1
CA $233
CA $273 total
includes taxes & fees
Jun 30 - Jul 1
8.6/10 Excellent! (2,944 reviews)
"Perfect area for walking around chicago even at night. Felt 100 percent safe and the weather mafe for an emalculat trip."
Reviewed on Jun. 4, 2024
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.
Explore other types of vacation packages
Frequently asked questions
Discover the most popular places to visit in Grand Boulevard
Elam House
You can learn about the history of Chicago when you stop by Elam House. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.
Harold Washington Cultural Center
You can enjoy some culture when you stop by Harold Washington Cultural Center in Chicago. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.
Dr. Daniel Hale Williams Residence
You can learn about the history of Chicago with a trip to Dr. Daniel Hale Williams Residence. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.
Things to do
Odyssey Lake Michigan Premier Dinner Cruise
CA $255
Per adult
76% of travellers recommend
Chicago: City Minibus Tour with Optional Architecture Cruise
CA $64
Per adult
98% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.