The Loop Holidays from £945

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,314, price is now £945 per person
£945
per person
27 Aug - 31 Aug
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
The front foyer had beautiful glass bulbs that were very dusty and dirty. Not a good first impression Housekeeping or room service could have been disclosed for 4 nights garbage build up Also notice we had no bathroom hooks to hang wet towels just one towel bar. Bed was comfortable and linens were fine. Oh and, $8 bottle of Voss water in room no cups in room or bathroom. Microwave breakfast 😑

Reviewed on 15 Jun 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £5,754, price is now £3,748 per person
£3,748
per person
1 Aug - 8 Aug
found 9 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (493 reviews)
If you drive, it’s very close to everything pretty much. It’s clean and nice to stay with family. Parking is a little expensive but that applies to most of Chicago area.

Reviewed on 14 Jun 2026

Great Wolf Lodge Illinois

Great Wolf Lodge Illinois

3 out of 5
Price was £2,341, price is now £1,694 per person
£1,694
per person
1 Aug - 8 Aug
found 9 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (1,003 reviews)
First time staying at a Great Wolf Lodge. Was a wonderful time. Onsite food selection was great and easy to order ahead of time if wanted. Waterpark was as expected. Many other activities available to keep the kids entertained was a nice touch. Arcade is expensive and having to pay to park were my only disappointments. Otherwise highly recommend!

Reviewed on 18 Jun 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,275, price is now £1,651 per person
£1,651
per person
9 Sept - 14 Sept
found 7 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.6/10 Exceptional! (1,888 reviews)
Very clean rooms, helpful staff and great amenities! Close to everything and convenient to shopping and eating Felt safe and comfortable in the area !

Reviewed on 15 Jun 2026

Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was £1,444, price is now £1,073 per person
£1,073
per person
8 Sept - 13 Sept
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (2,146 reviews)
I stayed one night on a business trip. The location was great and the hotel room very clean. The amenities are great, but i unfortunately was unable to take advantage. I had a little trouble sleeping with the bed not being all that comfortable and the city noise wasn’t something I’m used to. Overall though a nice hotel.

Reviewed on 17 Jun 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

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 £122 per night from 29 Jun to 30 Jun
£122
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (10,127 reviews)
"Great location for the hotel to be close where you want to go. Walking distance to the places we wanted to visits. We were there for 2026 Pokemongo Fest Chicago- Grant Park. So, it was an excellent location. Room had a view of the river/water. Room was very spacious for a standard double bed room ..."

Reviewed on 18 Jun 2026

Congress Plaza Hotel
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
Fully refundableReserve now, pay when you stay
The price is £109 per night from 5 Jul to 6 Jul
£109
5 Jul - 6 Jul
includes taxes & fees
7.6/10 Good! (2,609 reviews)
"Honestly this was an amazing find for a downtown Chicago stay. If you’re super picky about how the room looks and want something modern, this isn’t for you. If you want a great location, helpful staff, affordable rates, and sound proof walls, then this is your place."

Reviewed on 18 Jun 2026

Travelodge by Wyndham Downtown Chicago
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
200 North Columbus Drive Chicago IL
The price is £239 per night from 6 Jul to 7 Jul
£239
6 Jul - 7 Jul
includes taxes & fees
8.8/10 Excellent! (2,204 reviews)
"We stayed at the Fairmont in the King Gold Suite for my daughter’s college graduation ceremony weekend. The room was spacious to accommodate 3 adults. Excellent amenities, location, and service."

Reviewed on 17 Jun 2026

Fairmont Chicago at Millennium Park
See all 1,199 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
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Beach Holidays
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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.

Stay near popular The Loop attractions

Reflection of a Chicago buildings in a mirror of Chicago Bean, Millennium Park, Chicago city, USA., Shutterstock ID 1129809965, Purchase Order: SP-2109, Order Number: SP-2109 Qantas AU US Sale New Ads

Millennium Park

9.4/5 (30,446 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
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* 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.