Grand Boulevard Holidays from £1,167

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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
Price was £1,467, price is now £1,167 per person
£1,167
per person
11 May - 15 May
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
The place was beautiful. Breakfast was lovely and I enjoyed everything.

Reviewed on 10 Apr 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £2,086, price is now £1,674 per person
£1,674
per person
11 May - 15 May
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,123 reviews)
The staff at the Pendry are top notch. We arrived early and just wanted to drop our bags off, but the staff was able to check us in several hours early. Upon learning it was my birthday, the bell hop brought me a glass of wine from the bar and later, the staff sent up a bottle of prosecco and birthday cupcakes. Our room

Reviewed on 7 Apr 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £1,569, price is now £1,269 per person
£1,269
per person
11 May - 15 May
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Great location! Easy parking and the rooms were gorgeous! We will definitely stay here next time we visit Chicago

Reviewed on 10 Apr 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Price was £1,508, price is now £1,278 per person
£1,278
per person
11 May - 15 May
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Very friendly staff, great location.

Reviewed on 6 Apr 2026

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Price was £1,803, price is now £1,529 per person
£1,529
per person
11 May - 15 May
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,026 reviews)
Wonderful hotel. Great location at a great price.

Reviewed on 1 Apr 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

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 £108 per night from 26 Apr to 27 Apr
£108
26 Apr - 27 Apr
includes taxes & fees
8/10 Very Good! (10,081 reviews)
Good in general

Reviewed on 11 Apr 2026

Congress Plaza Hotel
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 £120 per night from 26 Apr to 27 Apr
£120
26 Apr - 27 Apr
includes taxes & fees
9/10 Wonderful! (4,100 reviews)
Recommend packing light if you self-park and walk to the hotel!

Reviewed on 11 Apr 2026

Hilton Chicago/Magnificent Mile Suites
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
Fully refundableReserve now, pay when you stay
The price is £135 per night from 30 Apr to 1 May
£135
30 Apr - 1 May
includes taxes & fees
8.6/10 Excellent! (5,833 reviews)
Perfect location for a family trip, the hotel amenities were amazing and the staff was very friendly. We did have an issue with having our room serviced during our stay, after a long day out we came back to it still not being serviced, after asking the front desk they said they would put in the request ...

Reviewed on 9 Apr 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,770 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 £1,167, 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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
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
Flyover in Chicago

Flyover in Chicago

£29
per adult
98% of travellers recommend
Flyover in Chicago
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.