Grand Boulevard Holidays from AU$3,689
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Your Grand Boulevard Holiday
Experience all the fabulous things this neighbourhood has to offer with a customised Grand Boulevard holiday package. However you imagine spending your days here, you'll find endless opportunities for adventure, relaxation and fun. Not sure what to do during your trip to Grand Boulevard? Nearby attractions like University of Chicago, Chicago Museum of Science and Industry and Guaranteed Rate Field are good places to start. Whatever your travel plans or the size of your budget, booking your ideal Grand Boulevard holiday is a cinch with Expedia.
The Latest Grand Boulevard Holiday Packages
- The Godfrey Hotel Chicago
28 Dec - 3 JanThe Godfrey Hotel Chicago + Flight
Downtown Chicago6 nights4.5 star property8.8/10 - Excellent (2,609 reviews)"I liked my stay with Godfrey , but furniture needs updating curtains need updating and the rooms are too small …. I love the window view of the city and the rooftop"Reviewed November 11, 2026Return • Sydney (SYD) - Chicago (ORD)SYD - ORD • 1 stop ORD - SYD • 1 stopAU$4,440AU$3,689found 15 hours agoper traveller - The Peninsula Chicago
28 Dec - 3 JanThe Peninsula Chicago + Flight
Downtown Chicago6 nights5.0 star property9.8/10 - Exceptional (1,012 reviews)Return • Sydney (SYD) - Chicago (ORD)SYD - ORD • 1 stop ORD - SYD • 1 stopAU$7,537AU$5,906found 15 hours agoper traveller - Swissotel - Chicago
28 Dec - 3 JanSwissotel - Chicago + Flight
Downtown Chicago6 nights4.5 star property9.0/10 - Wonderful (3,579 reviews)"Very good"Reviewed November 11, 2026Return • Sydney (SYD) - Chicago (ORD)SYD - ORD • 1 stop ORD - SYD • 1 stopAU$4,711AU$3,890found 15 hours agoper traveller - Arlo Chicago
28 Dec - 3 JanArlo Chicago + Flight
Downtown Chicago6 nights4.0 star property9.4/10 - Exceptional (2,425 reviews)Return • Sydney (SYD) - Chicago (ORD)SYD - ORD • 1 stop ORD - SYD • 1 stopAU$4,555AU$3,774found 15 hours agoper traveller - The Talbott, Autograph Collection
28 Dec - 3 JanThe Talbott, Autograph Collection + Flight
Downtown Chicago6 nights4.5 star property9.4/10 - Exceptional (199 reviews)Return • Sydney (SYD) - Chicago (ORD)SYD - ORD • 1 stop ORD - SYD • 1 stopAU$4,447AU$3,695found 15 hours agoper traveller
Our guide on where to stay in Grand Boulevard
Downtown Chicago
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Magnificent Mile
A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.
The Loop
Striking architecture, urban park space and countless entertainment options all make The Loop one of the most memorable spots in the city.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Discover the most popular places to visit in Grand Boulevard
What to do near Grand Boulevard
Skydeck Chicago at Willis Tower
Grand Boulevard Hotel Deals
Hilton Vacation Club Hotel Blake Chicago
Hilton Vacation Club Hotel Blake Chicago"Super friendly staff! Room was clean and updated. Beds were very comfortable. Will definitely stay here again."
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by Hilton
"Very good"
Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium Park
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
L7 CHICAGO by LOTTE HOTELS
L7 CHICAGO by LOTTE HOTELS"The room was spacious, clean and had everything we needed. The check in and check out process was quick and easy. The price was 10/10 and I'd stay there on my next trip."
Hyatt Place Chicago/River North
Hyatt Place Chicago/River NorthFrequently Asked Questions
How much does a Grand Boulevard holiday package cost?
Be ready to book, because a getaway to Grand Boulevard starts from an affordable AU$3,689. When you combine your flights, hotels and more into a holiday 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 holiday?
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 holiday 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 travelling 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 holiday 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 holiday package?
Yes you can, and we're here to help. You may be able to cancel or amend your Grand Boulevard holiday 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.