Grand Boulevard Holidays from £1,022

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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 Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
7 Sept - 13 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
8.2/10 Very Good! (1,785 reviews)
Would stay here again. Centrally located in the North loop with easy access to public transportation, good food, and events.

Reviewed on 29 Jun 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
12 Aug - 17 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,065 reviews)
Hotel room was nothing like the pictures when reserving the room. Bathroom was horrible. Shower was extremely small. I’m very petite & I barely fit in the shower. I had no counter space in bathroom to set my toothbrush or any other items. Ac barely cooled the room.

Reviewed on 30 Jun 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
12 Aug - 17 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Staff was very friendly and helpful. We had a great stay in every way possible!

Reviewed on 30 Jun 2025

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
per person
1 Aug - 6 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
A beatiful iconic property with super comfortable beds, great location for shopping and venues whether walking, using subways, ubers, or busses, awesome room views, and friendly front desk staff. We would feel better about the daily amenity fee if they offered good coffee in the room, or lobby.

Reviewed on 28 Jun 2025

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
per person
7 Sept - 13 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,034 reviews)
First time staying at the Viceroy and I was impressed! I will look for other Viceroy hotels when I travel! Very clean and accommodating!

Reviewed on 30 Jun 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

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 £123 per night from 6 Jul to 7 Jul
£123
6 Jul - 7 Jul
includes taxes & fees
8.8/10 Excellent! (2,343 reviews)
"It was good, clean and large room"

Reviewed on 27 Jun 2025

Hilton Chicago/Magnificent Mile Suites
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is £161 per night from 2 Jul to 3 Jul
£161
2 Jul - 3 Jul
includes taxes & fees
9/10 Wonderful! (1,932 reviews)
"Elevators were really slow like uncomfortably slow and not efficient at all so"

Reviewed on 29 Jun 2025

InterContinental Chicago Magnificent Mile by IHG
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 £86 per night from 1 Jul to 2 Jul
£86
1 Jul - 2 Jul
includes taxes & fees
7.8/10 Good! (8,883 reviews)
"Great staff!"

Reviewed on 28 Jun 2025

Congress Plaza Hotel
See all 4,462 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 £1,022, 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

£36
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£33
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

£33
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
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.