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 $4,200 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.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,578, price is now CA $1,025 per person
CA $1,025
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,019 reviews)
The place was spacious and well decorated. Location was great and staff was friendly. We did not use the amenities but the 6th floor was amazing! The two things that could be a lot better: shower pressure and blackout curtains. I am a very light sleeper and the room was filled with daylight as early as 4:45am in June. Shower had no pressure and very little water. Overall was a great stay!

Reviewed on Jun 15, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,838, price is now CA $1,230 per person
CA $1,230
per person
Sep 3 - Sep 6
found 20 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,127 reviews)
Beautiful hotel. Very clean which is very important to me. Couldn’t have asked for a more perfect location. Food and drink prices at the restaurant/bar were high. Other than that, would highly recommend.

Reviewed on Jun 16, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,631, price is now CA $1,896 per person
CA $1,896
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (493 reviews)
If you drive, it’s very close to everything pretty much. It’s clean and nice to stay with family. Parking is a little expensive but that applies to most of Chicago area.

Reviewed on Jun 14, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $2,406, price is now CA $1,755 per person
CA $1,755
per person
Aug 1 - Aug 5
found 18 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,325 reviews)
The staff was great. The room was nice but I would have preferred more towels. The remote in our room wasn’t working fully as well as the steamer in the room. Otherwise, it is a good hotel but would not recommend for families.

Reviewed on Jun 15, 2026

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was CA $2,235, price is now CA $1,664 per person
CA $1,664
per person
Sep 3 - Sep 6
found 12 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
The room was lovely and spacious. The bathroom was very nice. We ordered room service as well as had a drink and ate at the restaurant in the hotel and that was delicious.

Reviewed on Jun 15, 2026

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

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Grand Boulevard Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $191 per night from Jun 30 to Jul 1
CA $191
CA $227 total
Jun 30 - Jul 1
includes taxes & fees
8/10 Very Good! (10,289 reviews)
"Staff was very nice. Room was clean with a great view."

Reviewed on Jun 16, 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $191 per night from Jun 30 to Jul 1
CA $191
CA $227 total
Jun 30 - Jul 1
includes taxes & fees
7.8/10 Good! (1,594 reviews)
"Clean room staff nice"

Reviewed on Jun 15, 2026

The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $201 per night from Jul 1 to Jul 2
CA $201
CA $229 total
Jul 1 - Jul 2
includes taxes & fees
8.8/10 Excellent! (2,677 reviews)
"The room was clean and it was nice having a balcony. It was a little busy because Prom was happening but not too terribly bad. Would stay again. Beds comfortable."

Reviewed on Jun 16, 2026

Hyatt Regency O'Hare Chicago
See all 4,594 properties in Grand Boulevard
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Grand Boulevard vacation package cost?
Be ready to book, because a getaway to Grand Boulevard starts from an affordable CA $1,025. When you combine your flights, hotels and more into a vacation package, you'll enjoy the best bargains.
How do I get a cheap travel package to Grand Boulevard?
One of the easiest ways to save cash (and time) is to bundle your bookings with Expedia. Flights, hotels, activities and rental cars — we've got everything you need. Pick a combination that suits you and see your savings pile up. We know a package deal is never a one-size-fits-all. That's why we offer more than 550 air carriers and 1,000,000 properties from all over the world, which lets you customize your Grand Boulevard getaway.
Where should I stay in Grand Boulevard?
Most who travel to Grand Boulevard include University of Chicago and Chicago Museum of Science and Industry on their must-see lists. Why not choose a hotel near these popular attractions?
What are the top hotels in Grand Boulevard?
If it's comfort and convenience you'd like, it's hard to beat Amber Inn. Spend your nights kicking back here and your days wandering around Grand Boulevard's finest sights.
How far in advance should I book my Grand Boulevard vacation?
Your best bet is to book early. Airlines generally release flights around a year ahead of departure, and this is when you can pick up some of the cheapest prices. Just been told you need to take some vacation time in a few weeks? No sweat. Expedia are never short of fantastic bargains to send you on the getaway of your dreams, at a price you can afford.
What does an Expedia Grand Boulevard travel package include?
That depends on what you want. If you're traveling alone, you might decide to combine flights and hotels. Taking the whole family to Grand Boulevard? A travel package including rental cars, flights and hotels might suit you better. Expedia gives you the flexibility to tailor-make your travel package.
What should I know before booking a Grand Boulevard travel package?
So many places to travel to, so many things to see. With a package, you can check more of them off your list. Bundle your flights, rental cars and hotels and enjoy big savings.
Can I choose my airline with a Grand Boulevard Expedia vacation package?
You certainly can. We have more than 550 partner airlines worldwide, so choose the carrier that fits your travel preferences.
If I'm not able to travel, can I cancel my Grand Boulevard vacation package?
Yes you can, and we're here to help. You may be able to cancel or amend your Grand Boulevard vacation package for free within 24 hours of booking. However, you may incur a fee from your airline, hotel or car rental company if you booked more than 24 hours ago. If your travel plans suddenly change, visit our Customer Service Portal for more information.

Stay near popular Grand Boulevard attractions

Harold Washington Cultural Center

Enjoy an outing to Harold Washington Cultural Center during your stay in Chicago. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.