The Loop Holidays from £822

Book a Hotel + Flight or Car together to unlock savings

    deals illustration
    Better together
    Save up to £335 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

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.
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
Downtown Chicago
per person
31 Aug - 7 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.4/10 Very Good! (1,005 reviews)
We would stay here again!

Reviewed on 16 Jun 2025

Art Villa

Art Villa

4.5 out of 5
West Town
per person
1 Sept - 6 Sept
just found
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
No reviews
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
27 Aug - 3 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,034 reviews)
Very accommodating. All the staff were amazing! We will be back.

Reviewed on 15 Jun 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
1 Sept - 6 Sept
just found
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9/10 Wonderful! (612 reviews)
I thought this property was very nice and clean. However there were some complications with over booking and we didn’t get the 2 bedroom we booked but rather separate 1 bedrooms which I was sad about. Also the jacuzzi was kind of cold but I will say the staff was the nicest they could be. The rooms were pretty and modern

Reviewed on 15 Jun 2025

Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
Downtown Chicago
per person
31 Aug - 7 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.8/10 Excellent! (1,643 reviews)
Property has a nice skyline view but pricing and room Size definitely make it less appealing. Parking is not included, it’s an additional 60 dollars a night, some Of the elevators were down , waiting time was inconvenient. The staff was friendly, restaurant on 15th floor has really good wings and old fashions ! Overall , unsatisfied with stay and cleanliness of room.

Reviewed on 16 Jun 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 £87 per night from 1 Jul to 2 Jul
£87
1 Jul - 2 Jul
includes taxes & fees
7.8/10 Good! (8,891 reviews)
"It was good"

Reviewed on 15 Jun 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 £106 per night from 2 Jul to 3 Jul
£106
2 Jul - 3 Jul
includes taxes & fees
9.2/10 Wonderful! (3,187 reviews)
"Very cool and digitally efficient. Great bar and restaurant—best breakfast we’ve had in a competitive hotel. But tough on older people like us. We were given a ‘wheel chair room’ so we would not have a bed next to a wall. Lots of space there, but no place to put anything or sit. Never saw a regular ..."

Reviewed on 16 Jun 2025

citizenM Chicago Downtown
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £151 per night from 30 Jun to 1 Jul
£151
30 Jun - 1 Jul
includes taxes & fees
8.8/10 Excellent! (2,232 reviews)
"parking is expensive $87 for valet $70 for self"

Reviewed on 15 Jun 2025

Swissotel - Chicago
See all 1,229 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

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 featuring a river or creek, a bay or harbour and a city

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
Art Institute of Chicago which includes art and interior views

Art Institute of Chicago

4.5/5(66 reviews)

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

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago: Architecture Boat Tour with Drinks

Chicago: Architecture Boat Tour with Drinks

£31
per adult
96% of travellers recommend
Chicago: Architecture Boat Tour with Drinks
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