Grand Boulevard Holidays

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    Save up to S$134 when you book a flight and hotel together*

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Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was S$1,102, price is now S$943 per person
S$943
per person
30 Jan - 1 Feb
found 1 day ago
Return flight included
Seattle (SEA) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Jasmine was courteous and friendly, made our check in process smooth. Clean rooms and the breakfast was amazing. I definitely recommend staying here.

Reviewed on 31 Dec, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was S$1,539, price is now S$1,215 per person
S$1,215
per person
30 Jan - 1 Feb
found 1 day ago
Return flight included
Seattle (SEA) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Great time and staff

Reviewed on 30 Dec, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was S$1,118, price is now S$987 per person
S$987
per person
30 Jan - 1 Feb
found 1 day ago
Return flight included
Seattle (SEA) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.

Reviewed on 18 Dec, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was S$1,116, price is now S$988 per person
S$988
per person
30 Jan - 1 Feb
found 1 day ago
Return flight included
Seattle (SEA) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Everything was great!

Reviewed on 29 Dec, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was S$1,584, price is now S$1,424 per person
S$1,424
per person
30 Jan - 1 Feb
found 1 day ago
Return flight included
Seattle (SEA) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Emil was a fabulous server at the Lobby Restaurant. I think that’s his name. Tall guy. Becca at front desk also fantastic. The lady who checked us in not so good.

Reviewed on 29 Dec, 2025

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 which includes 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

Top hotels in Grand Boulevard

Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$247 per night from 11 Jan to 12 Jan
S$247
11 Jan - 12 Jan, 2026
includes taxes & fees
8.4/10 Very Good! (2,414 reviews)
Rooms were nice, staff friendly, enjoyed the indoor pool and hot tubs.

Reviewed on 26 Dec, 2025

Hilton Chicago
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 S$135 per night from 7 Jan to 8 Jan
S$135
7 Jan - 8 Jan, 2026
includes taxes & fees
8.8/10 Excellent! (3,572 reviews)
excellent

Reviewed on 26 Dec, 2025

Hilton Chicago/Magnificent Mile Suites
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$247 per night from 7 Jan to 8 Jan
S$247
7 Jan - 8 Jan, 2026
includes taxes & fees
8.4/10 Very Good! (2,194 reviews)
Staff was great. Christmas decor was amazing.

Reviewed on 29 Dec, 2025

Palmer House a Hilton Hotel
See all 4,749 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 holiday package cost?
Be ready to book, because a getaway to Grand Boulevard starts from an affordable S$943. 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.

Things to do

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

S$32
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

S$52
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Art Institute of Chicago

Art Institute of Chicago

S$52
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Chicago

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.