Grand Boulevard Holidays from £776

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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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
29 Sept - 3 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
We tried the Riu Rooftop bar and it was lovely. The buffet breakfast was great. However, the weekend start time was a bit late compared to weekday. We had to check out at 7:15 and missed it. Hotel staff did not allow or offer us a small bag of pastry to go before we check out even though the 3rd person breakfast was charged

Reviewed on 14 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
20 Sept - 25 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
It was totally worth the money as it had the best amenities, great views overlooking the city, and the river, staff was phenomenal, and couldn’t ask for more!

Reviewed on 15 Aug 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
29 Sept - 3 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
4 Oct - 11 Oct
found 7 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
The hotel is situated in Fulton market and has many options for dining. The bed was comfortable, but the linens were very wrinkled and the comforter had stains on it.

Reviewed on 15 Aug 2025

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
per person
17 Sept - 22 Sept
found 22 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (260 reviews)
Fantastic experience. Staff was friendly and accommodating. Highly recommend

Reviewed on 15 Aug 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 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

Top hotels in Grand Boulevard

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 £117 per night from 1 Sept to 2 Sept
£117
1 Sept - 2 Sept
includes taxes & fees
7.8/10 Good! (8,984 reviews)
"Great location! Quiet and comfortable room. Love the history and architectural charm of this classic Chicago Hotel! Exercise room was the best equipped I've used!"

Reviewed on 14 Aug 2025

Congress Plaza Hotel
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 £169 per night from 2 Sept to 3 Sept
£169
2 Sept - 3 Sept
includes taxes & fees
8.4/10 Very Good! (1,852 reviews)
"Pleasant experience. Accommodations were good. Surrounding area was convenient to shopping, eateries and p parks."

Reviewed on 13 Aug 2025

Palmer House a Hilton Hotel
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 £132 per night from 25 Aug to 26 Aug
£132
25 Aug - 26 Aug
includes taxes & fees
8.4/10 Very Good! (3,675 reviews)
"Hotel was quiet. Room was comfortable. Location was great."

Reviewed on 13 Aug 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 4,604 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
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Grand Boulevard travel package cost?
From as little as £776, 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.

Things to do

River tour boat in Chicago

Architecture River Tour

£31
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

£33
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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. Flight-inclusive packages are ATOL protected.