Grand Boulevard Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Grand Boulevard Vacation Packages
- Le Méridien Essex Chicago
Jan 21 - Jan 24Le Méridien Essex Chicago + Flight
Downtown Chicago3 nights4.0 star property9.0/10 - Wonderful (1,000 reviews)"I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything."Reviewed November 3, 2026Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • 1 stop ORD - YYZ • NonstopCA $914CA $671found 2 hours agoper traveller - The Peninsula Chicago
Jan 21 - Jan 24The Peninsula Chicago + Flight
Downtown Chicago3 nights5.0 star property9.8/10 - Exceptional (1,009 reviews)Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • 1 stop ORD - YYZ • Nonstop - Sheraton Grand Chicago Riverwalk
Dec 19 - Dec 23Sheraton Grand Chicago Riverwalk + Flight
Downtown Chicago4 nights4.0 star property8.6/10 - Excellent (1,885 reviews)Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • 1 stop ORD - YYZ • NonstopCA $1,395CA $992found 2 days agoper traveller - Park Hyatt Chicago
Jan 21 - Jan 24Park Hyatt Chicago + Flight
Downtown Chicago3 nights5.0 star property9.6/10 - Exceptional (1,003 reviews)Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • 1 stop ORD - YYZ • NonstopCA $1,801CA $1,316found 1 day agoper traveller - Pendry Chicago
Jan 21 - Jan 24Pendry Chicago + Flight
Downtown Chicago3 nights4.5 star property9.2/10 - Wonderful (1,164 reviews)"The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back."Reviewed November 8, 2026Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • 1 stop ORD - YYZ • NonstopCA $1,344CA $984found 1 day agoper traveller
Where to stay in Grand Boulevard
Downtown Chicago
Magnificent Mile
The Loop
River North
Lincoln Park
Discover the most popular places to visit in Grand Boulevard
What to do near Grand Boulevard
Skydeck Chicago at Willis Tower
Wendella's 90-min Chicago River Architecture Tour
Grand Boulevard Hotel Deals
Hilton Vacation Club Hotel Blake Chicago
Hilton Vacation Club Hotel Blake Chicago"Every thing is good!👍🌹"
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by Hilton"Upon arrival we were greeted immediately. The staff helped us unload our bags into a luggage cart and valet took the car to park. Our room was available for early check in. We stayed in the 7th floor in a single king room. Everything was clean and the views were great. We went up to the 22nd floor to see the river views from the rooftop bar. This hotel is in an absolute perfect location to see Chicago. You are close enough to walk to river walk, millennium park, the train, and magnificent mile....
Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium Park"The staff is so well-trained - professional, caring, friendly - a joy. An upscale hotel with a great breakfast restaurant in the morning, Room very comfortable."
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG"I had a great stay at this hotel! The experience was smooth, the room was comfortable, and everything was just what I needed. The staff was friendly, and I would definitely consider staying here again. Highly recommend!"
L7 CHICAGO by LOTTE HOTELS
L7 CHICAGO by LOTTE HOTELS"Great location, helpful staff. Would stay again."
Hyatt Place Chicago/River North
Hyatt Place Chicago/River NorthFrequently 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 $671. 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.