The Loop Holidays from £1,988

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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.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
14 Jul - 18 Jul
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (3,494 reviews)
Excellent quality. Comfortable bed, nice view from 12th floor over river. Friendly staff.

Reviewed on 11 May 2024

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
per person
14 Jul - 18 Jul
Return flight included
London (LHR) to Chicago (ORD)
8/10 Very Good! (1,783 reviews)
Check in slow, only 1 person at counter. Food under edge of bed. Have to register peloton.

Reviewed on 11 May 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
14 Jul - 18 Jul
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
Beautiful experience Top shelf everything This was my 4th stay here while visiting Chicago

Reviewed on 10 May 2024

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
per person
14 Jul - 18 Jul
Return flight included
London (LHR) to Chicago (ORD)
8.6/10 Excellent! (1,001 reviews)
We had a wonderful time in Chicago! This property was located in such a great area and easy walking to all the things we wanted to do...and eat. :)

Reviewed on 10 May 2024

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
Downtown Chicago
per person
14 Jul - 18 Jul
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (1,920 reviews)
Very clean and well maintained. It’s in a very busy location but convenient to walk around.

Reviewed on 12 May 2024

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

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

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 £125 per night from 13 May to 14 May
£125
per night
13 May - 14 May
7.6/10 Good! (6,705 reviews)
Great hotel to start Route 66 from
"A great hotel to start our Drive on Route 66. Perfectly located to see a lot of Chicago. Just need more lights in the room"

Reviewed on 11 May 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £152 per night from 27 May to 28 May
£152
per night
27 May - 28 May
8.6/10 Excellent! (2,864 reviews)
"We enjoyed our stay, great area within walking distance of shopping, food and activities. The room was clean and comfortable (standard room). The facility offers valet parking for a fee. The staff was friendly. The only downside was the small shower. Overall, I would recommend this hotel as a budget ..."

Reviewed on 11 May 2024

River 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 £149 per night from 27 May to 28 May
£149
per night
27 May - 28 May
9/10 Wonderful! (1,331 reviews)
"Would totally stay here again. Easy access to great food, museums and the Chicago River!"

Reviewed on 11 May 2024

citizenM Chicago Downtown
See all 1,274 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

Image for 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
Image for 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
Image for Art Institute of Chicago

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

Image for Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

£43
Per adult
92% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
Image for Chicago Pizza Tour

Chicago Pizza Tour

£59
Per adult
100% of travellers recommend
Chicago Pizza Tour
Image for Chicago: City Minibus Tour with Optional Architecture Cruise

Chicago: City Minibus Tour with Optional Architecture Cruise

£37
Per adult
98% of travellers recommend
Chicago: City Minibus Tour with Optional Architecture Cruise
See all activities in Chicago

More trip options

* 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.