Grand Boulevard Holidays from £969
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Your Grand Boulevard Holiday
Your next escape is calling your name with a holiday package to Grand Boulevard. Fun, food and nonstop good times — you're sure to find it in this neighbourhood. Eager to explore the sights during your trip to Grand Boulevard? Be sure to check out nearby attractions like University of Chicago, Chicago Museum of Science and Industry and Guaranteed Rate Field. Whatever your ideal Grand Boulevard holiday looks like, you can make it a reality with Expedia.
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
£1,460
per person
20 Nov - 26 Nov
found 22 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
The Trump hotel is right in the middle of downtown, but it's on the quieter side of the river from the other hotels. It offers direct access to the river where you can join the architecture river tour and is overall quieter than the hotels on the other side of the river. The self parking is a bit of a tricky drive up very narrow and curving ramps. If you drive a Suburban or a Cybertruck, you might have difficulty.
Reviewed on 29 Sept 2026
Level Chicago – Old Town
Downtown Chicago
£1,053
per person
19 Nov - 24 Nov
found 7 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (527 reviews)
The location is perfect and the building is quite nice. The rooms are also comfortable. This is not a hotel, but rather occupies several floors in a large apartment building. We had a couple issues with our room (malfunctioning, smoke alarm and empty body wash) and neither were dealt with despite a asking multiple times.
Reviewed on 27 Sept 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
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.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
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.
Top hotels in Grand Boulevard
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
£167
25 Oct - 26 Oct
includes taxes & fees
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£132
25 Oct - 26 Oct
includes taxes & fees
8/10 Very good! (10,282 reviews)
"Unable to adjust temperature control in room. Only a low, medium and high! Other than this, no complaints. Very convenient for Bears game."
Reviewed on 29 Sept 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
£161
25 Oct - 26 Oct
includes taxes & fees
8/10 Very good! (2,389 reviews)
"We got married here when it was Public Chicago 10 years ago. It’s gone downhill since. The room was not well maintained, they need to be updated. There were stains on the comforter. The shower was very hard to turn on. The pull out couch was very uncomfortable however our bed was very comfortable. ..."
Reviewed on 29 Sept 2026
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 travel package cost?
From as little as £969, you can create your own Grand Boulevard package. Simply combine hotels, flights and rental cars and we'll reward you with discounts.
If I'm not able to travel, can I cancel my Grand Boulevard travel package?
Your situation can change unexpectedly, so yes, you can. You may be able to cancel and rebook your Grand Boulevard travel package for free if you've booked in the last 24 hours. For bookings older than that, you can still make the necessary changes, but your car rental company, airline or hotel may impose a charge. Want more information? Check out our Customer Service Portal. We'll help make sure your trip goes off without a hitch.
How do I get a cheap travel package to Grand Boulevard?
Think of all the thrilling things you could do in Grand Boulevard with extra cash in your wallet. Watch your savings stack up when you combine your hotel and flights into a Grand Boulevard travel package. You have plenty of choice with Expedia too. In fact, you can take your pick of over 550 air carriers and 1,000,000 properties across the globe. Whether you're holidaying with the entire family or embarking on a solo adventure, organising a getaway to Grand Boulevard is better with a package.
Does Expedia offer Book Now, Pay Later Grand Boulevard holidays?
Your bank balance shouldn't get in the way of taking a holiday, so Expedia has worked out a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book a dream getaway without eating away at your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your trip. Consider one of these flexible payment options:
- Pay monthly holidays: Klarna has manageable monthly payment plans that work for all types of budgets, so you can escape on that well-deserved holiday now.
- Pay in instalments holidays: Into the idea of paying down your holiday in multiple transactions? Consider this Book Now, Pay Later option with Klarna.
- Low deposit holidays: If paying a small percentage of your trip (rather than the full total upfront) makes it easier to hit that "book now" button, opt for a low deposit holiday payment plan with Klarna.
Where should I stay in Grand Boulevard?
A journey to Grand Boulevard isn't over until you've seen Millennium Park and Wrigley Field. Book somewhere within walking distance so you can easily access these impressive tourist attractions.
What are the top hotels in Grand Boulevard?
If it's your first time staying in Grand Boulevard, reserve a room at Hyatt Regency Chicago or The Godfrey Hotel Chicago. Both hotels offer friendly service and are top options with lots of travellers.
How far in advance should I book my Grand Boulevard holiday?
While not all airlines advertise tickets early, it's usually possible to look up international fares on Expedia up to a year in advance. This is the time you'll bag some incredible bargains. If you've left everything to the last minute, you might still be in luck. Discounted prices occasionally become available a few weeks before departure.
What does an Expedia Grand Boulevard travel package include?
It depends on what sort of escape you have in the works. Grand Boulevard travel deals can include hotels, flights and car rentals. You can mix and match to find the travel package that suits your needs. You can also add on experiences and activities after you've booked to score even bigger discounts.
What should I know before booking a Grand Boulevard travel package?
You can save a tidy sum by bundling your flights, hotels and rental cars. Once you've made your booking, add on fun stuff like activities or tours. Your next unforgettable adventure is only a few clicks away.
Can I choose my airline with a Grand Boulevard Expedia travel package?
Definitely. Expedia has more than 550 partner airlines to pick from around the globe. With such a huge range of choice, finding the right carrier to whisk you off to Grand Boulevard shouldn't be hard.
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.
Robert S. Abbott Residence
Learn about the local history of Chicago with a stop at Robert S. Abbott Residence. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.
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.
Chicago Defender Original Site
You can learn about the history of Chicago when you stop by Chicago Defender Original Site. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.
Oscar S. De Priest Residence
Find out about the history of Chicago when you spend time at Oscar S. De Priest Residence. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.
Dr. Daniel Hale Williams Residence
You can learn about the history of Chicago with a trip to Dr. Daniel Hale Williams Residence. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.
Nat King Cole Residence
Find out about the history of Chicago when you spend time at Nat King Cole Residence. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.
Savoy Ballroom Site
Learn about the local history of Chicago when you spend time at Savoy Ballroom Site. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.
Things to do
Skydeck Chicago at Willis Tower
£32
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.