The Loop Holidays from £851
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
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.
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
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.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
West Loop
Consider a visit to The Old Post Office and take some time to enjoy the abundant dining options during your time in West Loop. If you want to see more of the city, jump on the metro at Racine Station or Ogilvie Transportation Center.
Top hotels in The Loop
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
£155
20 Sept - 21 Sept
includes taxes & fees
8.8/10 Excellent! (5,432 reviews)
"Location is great."
Reviewed on 17 Sept 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£154
27 Sept - 28 Sept
includes taxes & fees
8/10 Very good! (10,264 reviews)
"Clean room, funky smell tho. Super nice staff. Very helpful"
Reviewed on 17 Sept 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
£217
25 Sept - 26 Sept
includes taxes & fees
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.
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.
Stay near popular The Loop attractions
Photo by TM
Millennium Park
9.4/10 (30,446 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Photo by TM
Chicago Riverwalk
9.6/10 (13,574 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.
Willis Tower
9.0/10 (9,893 reviews)
Visit the Skydeck and gaze down over the Chicago cityscape from a dazzling 1,353 feet above the sidewalk.
Art Institute of Chicago
9.4/10 (7,898 reviews)
Explore a massive collection of works celebrating different cultures and historical times, from ancient Egypt to modern installations.
Photo by © Choose Chicago
Chicago Theatre
9.0/10 (1,866 reviews)
See a stage show at this iconic cultural beacon, which still captures all the splendor of a trip to the movie theater in the early 20th century.
Cloud Gate
9.4/10 (104 reviews)
You can learn about the history of Chicago with a visit to Cloud Gate. Discover the fascinating museums and notable monuments in this vibrant area.
Buckingham Fountain
9.2/10 (1,301 reviews)
This enormous art deco installation gives free regular water and light shows symbolizing the power and might of Lake Michigan.
Chicago City Hall
9.0/10 (10 reviews)
Chicago City Hall is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or experience the entertainment choices in this vibrant area.
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
£35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
£18
per adult
90% of travellers recommend
Explore a world of travel with Expedia
- 3 Star Hotels in The Loop
- 4 Star Hotels in Chicago
- 5 Star Hotels in Chicago
- Serviced Apartments in Chicago
- Condo Rentals in Chicago
- Hostels in Chicago
- Sports Hotels in Chicago
- All-Inclusive Hotels in Chicago
- Beach Resorts & in Chicago
- Boutique Hotels in Chicago
- Cheap Hotels in Chicago
- Casino Hotels in Chicago
- Family-Friendly Hotels in Chicago
- Gay-Friendly Hotels in Chicago
- Historic Hotels in Chicago
- Hotels Suites in Chicago
- Hotels with Connecting Rooms in Chicago
- Hotels with Parking in Chicago
- Hotels with Gym in Chicago
- Hotels with Parking in Chicago
- Hotels with Balcony in Chicago
- Hotels with Hot Tubs in Chicago
- Hotels with Indoor Pools in Chicago
- Hotels with Pool in Chicago
- Hotels with smoking rooms in Chicago
- Lakeside Hotels in Chicago
- Luxury Hotels in Chicago
- Pet-Friendly Hotels in Chicago
- Riverside Hotels in Chicago
- Romantic Hotels in Chicago
- Spa Hotels in Chicago
- Hotels with Waterpark in Chicago
- Chicago Hotels
- Hotels near Chicago Union Station
- Cheap Hotels in Downtown Chicago
- Hilton Hotels in Downtown Chicago
- Hotels Suites in Downtown Chicago
- Hotels with a View in Downtown Chicago
- Downtown Chicago Hotels
- Hotels near Grant Park
- Hotels near House of Blues Chicago
- Magnificent Mile Hotels
- Hotels near McCormick Place
- Hotels near Michigan Avenue
- Hotels near Millennium Park
- Hotels near Navy Pier
- Hotels near Northwestern Memorial Hospital
- River North Hotels
- Boutique Hotels in The Loop
- Cheap Hotels in The Loop
- The Loop Hotels
- West Loop Hotels
- Flights to Chicago
- American Airlines Dublin (DUB) to Chicago (ORD) flights
- Flights from Chicago
- Flights from Dublin (DUB) to Chicago (ORD)
- Flights from Edinburgh (EDI) to Chicago (ORD)
- Flights from Glasgow (GLA) to Chicago (ORD)
- Flights from London (LHR) to Chicago (ORD)
- Flights from Manchester (MAN) to Chicago (ORD)
- Art Institute of Chicago
- Blue Island Holidays
- Visit Downtown Chicago
- Chicago Harbor Lighthouse
- Visit Magnificent Mile
- Chicago Riverwalk
- Visit The Loop
- Chicago Theatre
- Chicago Water Tower
- Chicago Holidays
- Visit Chicago
- Cibc Theatre
- Cicero Holidays
- Downtown Chicago Holidays
- Ernest Hemingway Museum and House
- Garfield Park Conservatory
- Grant Park
- Hillside Holidays
- Lakeview Holidays
- Lincoln Hall
- Lincoln Park Conservatory
- Lincoln Park Zoo
- Lincoln Park Holidays
- Michigan Avenue
- Millennium Park
- Montrose Beach
- Navy Pier
- Northwestern University
- Robie House
- Shops at North Bridge
- Unity Temple
- Willis Tower
- Wrigley Field
* 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.