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 $1,887, price is now CA $1,262 per person
CA $1,262
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,019 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.

Reviewed on Jun 19, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,999, price is now CA $1,337 per person
CA $1,337
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.

Reviewed on Jun 11, 2026

Great Wolf Lodge Illinois

Great Wolf Lodge Illinois

3 out of 5
Price was CA $2,088, price is now CA $1,422 per person
CA $1,422
per person
Aug 2 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
8.6/10 Excellent! (1,003 reviews)
Kids had fun, it was a great stay.

Reviewed on Jun 19, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,849, price is now CA $1,308 per person
CA $1,308
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,127 reviews)
We were celebrating an anniversary. We had a greay stay. It was close to all the shopping and restaurants, staff were great and helpful. We will be back again!

Reviewed on Jun 18, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,617, price is now CA $1,914 per person
CA $1,914
per person
Aug 2 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (493 reviews)
There charges are not clear, unnecessary security deposit, long hold period and I don't even know if they refunded my security deposit as haven't received any bill/receipt post checkout

Reviewed on Jun 18, 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 $193 per night from Jun 29 to Jun 30
CA $193
CA $229 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,135 reviews)
"Thank you for everything"

Reviewed on Jun 19, 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 refundable
The price is CA $182 per night from Jun 29 to Jun 30
CA $182
CA $217 total
Jun 29 - Jun 30
includes taxes & fees
7.8/10 Good! (1,597 reviews)
"Beautiful facility! I loved Chicago which was my first time here. The staff were very nice!"

Reviewed on Jun 19, 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 $191 per night from Jun 28 to Jun 29
CA $191
CA $218 total
Jun 28 - Jun 29
includes taxes & fees
8.8/10 Excellent! (2,676 reviews)
"It’s our go-to place near the O’Hare Airport. Clean, safe, great amenities and friendly staff. I like the newly renovated rooms, too. No complaints!"

Reviewed on Jun 19, 2026

Hyatt Regency O'Hare Chicago
See all 4,716 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 $1,262. 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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River and Lake Cruise

CA $69
per adult
94% of travellers recommend
Chicago By Night River and Lake Cruise
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.