Grand Boulevard Holidays from AU$2,151

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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.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was AU$3,014, price is now AU$2,151 per person
AU$2,151
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (2,052 reviews)
I had an amazing experience here! The staff—from valet to front desk to restaurant—was incredibly courteous, and Nate at the bar was a standout! My room was spotless, housekeeping was proactive, and guest services were top-tier. The area around the hotel is packed with restaurants, bars, and convenience stores—super walkable and fun. Only two minor cons: the terrace closes at 10 PM (wish it stayed open later), and the pool was closed during my visit. Still, this place blew me away. Highly recommend!

Reviewed on 31 Aug. 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$4,113, price is now AU$2,534 per person
AU$2,534
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on 22 Aug. 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$5,610, price is now AU$3,478 per person
AU$3,478
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump

Reviewed on 29 Aug. 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was AU$3,233, price is now AU$2,223 per person
AU$2,223
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on 27 Aug. 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was AU$3,119, price is now AU$2,227 per person
AU$2,227
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (672 reviews)
Loved everything about it and the area.

Reviewed on 30 Aug. 2025

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 featuring a city

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$354 per night from 15 Sept to 16 Sept
AU$354
15 Sept - 16 Sept
includes taxes & fees
Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
The price is AU$302 per night from 3 Sept to 4 Sept
AU$302
3 Sept - 4 Sept
includes taxes & fees
Embassy Suites by Hilton Chicago Downtown River North
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$285 per night from 3 Sept to 4 Sept
AU$285
3 Sept - 4 Sept
includes taxes & fees
Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 4,735 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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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$2,151. 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.

Activities

River tour boat in Chicago

Architecture River Tour

AU$63
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

AU$69
per adult
96% of travellers recommend
Chicago By Night River & 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.