The Loop Holidays from £1,169

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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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £1,484, price is now £1,169 per person
£1,169
per person
13 Jun - 17 Jun
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great and helpful staff very clean, a place where you don’t feel out of place

Reviewed on 25 Apr 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,575, price is now £1,757 per person
£1,757
per person
16 Jun - 23 Jun
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
Thank you to Javon who was super helpful in our check in . The staff was so nice and accommodating. Additional linens were delivered in less than 5 minutes and then even extended our check out to 1pm. I will definitely be back when I’m in Chicago to try to catch fireworks. Our corner room was outstanding and breathtaking

Reviewed on 3 May 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £3,072, price is now £2,138 per person
£2,138
per person
16 Jun - 23 Jun
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (1,851 reviews)
The staff was excellent and extremely helpful and informative. The hotel has amazing amenities and location is great!

Reviewed on 3 May 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £2,518, price is now £1,876 per person
£1,876
per person
16 Jun - 23 Jun
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (1,124 reviews)
Great staff and perfect place to be in the middle of everything!

Reviewed on 27 Apr 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was £1,701, price is now £1,341 per person
£1,341
per person
13 Jun - 17 Jun
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (3,670 reviews)
Very clean room, kind and courteous staff. Would definitely stay again!

Reviewed on 3 May 2026

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

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.

Find hotels in Downtown Chicago

Top hotels in The Loop

River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is £107 per night from 26 May to 27 May
£107
26 May - 27 May
includes taxes & fees
8.8/10 Excellent! (5,159 reviews)
Staff was very friendly!

Reviewed on 3 May 2026

River Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
Fully refundable
The price is £86 per night from 26 May to 27 May
£86
26 May - 27 May
includes taxes & fees
8.8/10 Excellent! (3,485 reviews)
.

Reviewed on 4 May 2026

Club Quarters Hotel, Central Loop, Chicago
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 £110 per night from 8 May to 9 May
£110
8 May - 9 May
includes taxes & fees
8/10 Very Good! (10,147 reviews)
.

Reviewed on 4 May 2026

Congress Plaza Hotel
See all 1,244 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

Millennium Park

4.5/5(147 reviews)

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

Millennium Park
Chicago Riverwalk

Chicago Riverwalk

4.5/5(29 reviews)

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
Willis Tower

Willis Tower

4.5/5(81 reviews)

Visit the Skydeck and gaze down over the Chicago cityscape from a dazzling 1,353 feet above the sidewalk.

Willis Tower

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
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

Explore a world of travel with Expedia

* 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.