Grand Boulevard Vacations from ￥317,022

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥109,000 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

The Latest Grand Boulevard Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

3 out of 5
Price was ￥356,392, price is now ￥317,022 per person
￥317,022
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,073 reviews)
If going to Allstate for any reason best affordable stay

Reviewed on Oct 26, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥518,514, price is now ￥456,260 per person
￥456,260
per person
Jan 3 - Jan 9
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)
Clean, modern, up-to-date, and a great location. Would recommend.

Reviewed on Oct 27, 2026

Hilton Rosemont Chicago O'Hare

Hilton Rosemont Chicago O'Hare

3.5 out of 5
Price was ￥462,301, price is now ￥407,801 per person
￥407,801
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
Loved this hotel and will stay again.

Reviewed on Oct 26, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was ￥515,734, price is now ￥459,628 per person
￥459,628
per person
Jan 3 - Jan 9
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
This place is great and clean

Reviewed on Oct 26, 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was ￥552,384, price is now ￥494,025 per person
￥494,025
per person
Jan 3 - Jan 9
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
Wonderful stay, super clean and staff was verybhelpful

Reviewed on Oct 26, 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
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 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 ￥16,391 per night from Nov 22 to Nov 23
￥16,391
￥19,488 total
Nov 22 - Nov 23
includes taxes & fees
8/10 Very Good! (10,118 reviews)
"The rooms were really small and it could use some updating for sure however it did have a vintage feel and really nice restaurant and bar with very nice staff. Parking was expensive and on a different block which was inconvenient"

Reviewed on Oct 27, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥19,066 per night from Nov 22 to Nov 23
￥19,066
￥22,666 total
Nov 22 - Nov 23
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥18,197 per night from Nov 23 to Nov 24
￥18,197
￥21,634 total
Nov 23 - Nov 24
includes taxes & fees
8.8/10 Excellent! (5,575 reviews)
"Not the greatest property, outdated"

Reviewed on Oct 26, 2026

River Hotel
See all 4,705 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.

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 ￥317,022. 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.

Stay near popular Grand Boulevard attractions

Harold Washington Cultural Center

Enjoy an outing to Harold Washington Cultural Center during your stay in Chicago. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥3,812
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

￥6,275
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

￥6,642
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
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.