Grand Boulevard Holidays from AU$2,350

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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.

Top Holiday Package Deals in Grand Boulevard

Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago O'Hare Rosemont

Embassy Suites by Hilton Chicago O'Hare Rosemont

4 out of 5
Price was AU$2,631, price is now AU$2,350 per person
AU$2,350
per person
2 Sept - 9 Sept
found 1 day ago
Return flight included
Sydney (SYD) to Chicago (ORD)
8.8/10 Excellent! (1,429 reviews)
Room was clean. Breakfast was great. Site was close to entertaining area with many restaurants, movies.

Reviewed on 25 June 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was AU$4,209, price is now AU$3,029 per person
AU$3,029
per person
2 Sept - 9 Sept
found 1 day ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!

Reviewed on 25 June 2026

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was AU$3,531, price is now AU$2,856 per person
AU$2,856
per person
2 Sept - 9 Sept
found 1 day ago
Return flight included
Sydney (SYD) to Chicago (ORD)
8.4/10 Very good! (2,349 reviews)
Clean room, staff were very helpful and very friendly. Restaurants and bar were on point. Great experience! Thanks Hilton Chicago O’Hare Airport!

Reviewed on 25 June 2026

Hilton Rosemont Chicago O'Hare

Hilton Rosemont Chicago O'Hare

3.5 out of 5
Price was AU$3,117, price is now AU$2,689 per person
AU$2,689
per person
2 Sept - 9 Sept
found 1 day ago
Return flight included
Sydney (SYD) to Chicago (ORD)
8.4/10 Very good! (1,004 reviews)
The stay was good, the service at the restaurant was excellent.

Reviewed on 23 June 2026

Courtyard by Marriott Chicago O'Hare

Courtyard by Marriott Chicago O'Hare

3 out of 5
Price was AU$2,768, price is now AU$2,470 per person
AU$2,470
per person
2 Sept - 9 Sept
found 1 day ago
Return flight included
Sydney (SYD) to Chicago (ORD)
8.4/10 Very good! (1,015 reviews)
Todo bien solo la piscina estuvo cerrada el fin de semana

Reviewed on 22 June 2026

Our guide on 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

Our pick of the best 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 AU$235 per night from 29 June to 30 June
AU$235
29 June - 30 June
includes taxes & fees
8/10 Very good! (10,129 reviews)
"Great experience! Close to everywhere we wanted to go!"

Reviewed on 26 June 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$275 per night from 6 July to 7 July
AU$275
6 July - 7 July
includes taxes & fees
9/10 Wonderful! (4,459 reviews)
"Did a turn and burn stay here (checked in Saturday and checked out Monday) and had a pleasant visit. The front desk customer service was A+. My only 2 feedback are: the valet attendant should be more attentive. I waited 10 mins while the valet attendant was chatting away with a co-worker and then ..."

Reviewed on 26 June 2026

Hilton Chicago/Magnificent Mile Suites
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$349 per night from 5 July to 6 July
AU$349
5 July - 6 July
includes taxes & fees
9.4/10 Exceptional! (4,539 reviews)
"The hotel room cleanliness is of a very high standard. The complementary breakfast is extraordinary with a different majority of food and with a good procedure to take care of guests. The rooftop bar was sophisticated and attracts high class clientele. The room space is big enough to feel comfortable. ..."

Reviewed on 25 June 2026

Hotel Riu Plaza 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.
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Frequently 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$2,350. 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.

Stay near popular Grand Boulevard attractions

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.
See properties

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

AU$56
per adult
92% of travellers recommend
Art Institute of Chicago
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

AU$64
per adult
100% of travellers recommend
Chicago Sightseeing 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.