The Loop Holidays from £796

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Your The Loop Holiday

Lose yourself in the magic of this food-lovers neighbourhood with a The Loop holiday package. From its bars and pubs and history to its festivals, there's lots here for every traveller. Kick start your trip to The Loop with a visit to nearby attractions such as Millennium Park, Willis Tower and Art Institute of Chicago. Expedia is here to help put your plans into action. Book your ideal The Loop holiday now.

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
3 Oct - 7 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
The stay so far has been great, but we attempted to order in room dining which, according to the menu, is available until 5AM, but were advised by the front desk staff that we would not be able to order food for at least 40 minutes while the kitchen was “cleaned”. No other solutions were provided and we were very disappointed in this interaction.

Reviewed on 30 Jul 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
3 Oct - 7 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Great stay :) Mr 47 didn’t disappoint

Reviewed on 1 Aug 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
3 Oct - 7 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on 22 Jul 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
per person
10 Sept - 15 Sept
found 22 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (261 reviews)
walkable to many desireable places.

Reviewed on 16 Jul 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
3 Oct - 7 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (652 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).

Reviewed on 27 Jul 2025

Where to stay in The Loop

Find the best The Loop areas and neighborhoods for the activities you enjoy most. Learn more about The Loop
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 The Loop

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 £119 per night from 21 Aug to 22 Aug
£119
21 Aug - 22 Aug
includes taxes & fees
7.8/10 Good! (8,938 reviews)
"Very convenient location. Easy check-in, even with a very crowded lobby. Polite staff."

Reviewed on 1 Aug 2025

Congress Plaza Hotel
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £139 per night from 26 Aug to 27 Aug
£139
26 Aug - 27 Aug
includes taxes & fees
9.2/10 Wonderful! (3,491 reviews)
"I loved my stay at CitizenM Chicago. The staff was great, as well as the location of the hotel! Will definitely be coming back!"

Reviewed on 1 Aug 2025

citizenM Chicago Downtown
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £208 per night from 1 Sept to 2 Sept
£208
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (3,323 reviews)
"Hotel staff, from reception desk, to housekeeping, wait staff, to door staff were superb: helpful and very responsive throughout my stay."

Reviewed on 1 Aug 2025

Hyatt Regency Chicago
See all 1,281 properties in The Loop
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

Why should I book my The Loop holiday with Expedia?
With great-value airfares, hotel and car hire options all in one place, Expedia makes planning your The Loop getaway easy. Plus, we can help you bundle your bookings into a package holiday so you can get even more savings. Pick from awesome retreats, add your flights and/or a car hire (and maybe also some exciting activities!) and score unbeatable prices. Had a change of plans? Expedia offers a flexible cancellation policy for many bookings. To find out more, make your way to our Customer Service Portal link.
What are the top hotels for my holiday in The Loop?
Get your trip off to a great start by locking in a room at Canopy by Hilton Chicago Central Loop. It's one of the most sought-after properties for guests who want to be near The Loop. Another option close by is Hilton Garden Inn Chicago Central Loop.
How do I get a cheap holiday to The Loop?
Creating your own The Loop holiday with Expedia is an easy way to save. We have over 400 partner airlines and 321,000 hotel options spread across the globe. With such a fantastic range to select from, you'll have no trouble putting together your dream holiday. Learn more about how you can save money on your holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my The Loop holiday?
Make sure your holiday in The Loop is a memorable one by exploring its leading attractions. McCormick Place, Millennium Park, Art Institute of Chicago and Soldier Field are just some of the things you must see while you're in the city.
What is the best area to stay in when on holiday in The Loop?
There's lots to explore in The Loop, so stay close to its top sights and treat yourself to more time sightseeing. Millennium Park is one place to put on your to-do list.
Do I need a visa for my The Loop holiday?
Check the latest information on official government websites. Your nationality and whether you're travelling for work or pleasure will determine if you require a visa for The Loop. Familiarise yourself with the application process, including any required documentation, fees and turnaround times. Finalise your application well in advance to allow plenty of time for processing. Some visas may take weeks or even months to go through, depending on the country and time of year.
What should I wear on my The Loop holiday?
First, think about the types of activities you'll be doing during your The Loop trip and select versatile pieces that can be mixed and matched. For fashion inspiration or information on any dress codes, browse style blogs or social media accounts.
What does an Expedia The Loop holiday include?
With Expedia, you can select a combination of car hires, flights and hotels to create your ideal The Loop package. Once you've made your booking, simply add on all the fun stuff like tours and experiences. Don't forget — the more you bundle, the more pounds you'll save! Expedia has all sorts of properties, with the most in-demand in The Loop including apartments and private holiday homes. Whatever retreat you're after, Expedia allows for the flexibility to customise your holiday.
Does Expedia offer Book Now, Pay Later The Loop holidays?
Expedia has joined forces with online lender Klarna to make your next trip easier on your hip pocket. Paying in instalments means you can spread the costs of your next adventure, leaving you with more money to spend while you're away. Klarna has several payment plans to pick from, so you're sure to find one that falls within your budget. Browse these flexible payment options:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's convenient monthly instalment plans. If making small repayments each month works for you, pick this option at checkout.
  • No-deposit holidays: Hitting the "book now" button is easier with this payment option. With no upfront fee for your escape, you can Book Now, Pay Later and start working on your travel itinerary.

Can I choose my airline with a The Loop Expedia holiday?
Most definitely. Expedia has more than 400 partner airlines to choose from across the world. With so many choices, finding the ideal carrier to bring you to The Loop will be a cinch.

Popular places to visit

Millennium Park which includes autumn colours, modern architecture and street scenes

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Chicago Riverwalk featuring a river or creek, a bay or harbour and a city

Chicago Riverwalk

Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.

Chicago Riverwalk
Art Institute of Chicago which includes art and interior views

Art Institute of Chicago

Explore a massive collection of works celebrating different cultures and historical times, from ancient Egypt to modern installations.

Art Institute of Chicago

Things to do

River tour boat in Chicago

Architecture River Tour

£31
per adult
96% of travellers recommend
Architecture River Tour
Couple on a sightseeing boat in Chicago

Skyline Lake Tour

£22
per adult
92% of travellers recommend
Skyline Lake Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

£33
per adult
100% of travellers recommend
Chicago Sightseeing River and 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.