South Loop Holidays from £746

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Your South Loop Holiday

Take the stress out of travel planning with a South Loop holiday package. With everything locked in before you go, all you have to do is simply enjoy this commercial neighbourhood's cafes, bars and pubs and history. When it's time to sightsee, you'll find plenty of popular attractions nearby including Millennium Park, Willis Tower and Art Institute of Chicago. Visit one, two or all during your trip to South Loop. No matter your travel plans or the size of your budget, booking the ultimate South Loop holiday has never been easier with Expedia.

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was £930, price is now £746 per person
£746
per person
20 Jan - 24 Jan
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,419 reviews)
Great hotel in a prime location. Amazing customer service. Rooms were great although a little small. I would highly recommend this property.

Reviewed on 2 Nov 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,077, price is now £820 per person
£820
per person
2 Dec - 9 Dec
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.4/10 Very good! (3,148 reviews)
K

Reviewed on 1 Nov 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £1,087, price is now £836 per person
£836
per person
20 Jan - 24 Jan
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £1,233, price is now £959 per person
£959
per person
20 Jan - 24 Jan
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was £956, price is now £773 per person
£773
per person
20 Jan - 24 Jan
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)

Where to stay in South Loop

Find the best South Loop areas and neighborhoods for the activities you enjoy most. Learn more about South Loop
A busy city street with tall buildings, a bus, and cars.

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 South 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 £103 per night from 10 Nov to 11 Nov
£103
10 Nov - 11 Nov
includes taxes & fees
Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is £118 per night from 27 Nov to 28 Nov
£118
27 Nov - 28 Nov
includes taxes & fees
8.6/10 Excellent! (3,508 reviews)
"Staff was very helpful and the rooms were clean and affordable."

Reviewed on 1 Nov 2026

Hilton Chicago
Sentral Michigan Avenue

Sentral Michigan Avenue

4 out of 5
808 SOUTH MICHIGAN AVENUE Chicago IL
Fully refundableReserve now, pay when you stay
The price is £119 per night from 22 Nov to 23 Nov
£119
22 Nov - 23 Nov
includes taxes & fees
9/10 Wonderful! (1,399 reviews)
"We had a unit facing east, was a wonderful apartment overlooking Lake Michigan, and it exceeded all our expectations. The kitchen had everything we needed, the beds were comfortable, and we even did laundry during our trip. I had numerous requests when I first arrived--extra blankets, a few more ..."

Reviewed on 1 Nov 2026

Sentral Michigan Avenue
See all 4,683 properties in South 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

How much does a South Loop travel package cost?
Chart your own course with our South Loop travel packages, which start from just £746. Select the hotels and flights that suit your plans. Then, add on some activities or tours for an unforgettable adventure.
If I'm not able to travel, can I cancel my South Loop travel package?
Yes, you can. We totally understand that even the best-laid plans can fail, so we're here to help if you need to make changes to your South Loop travel package. It may be possible to cancel or amend your itinerary at no cost if you've booked within 24 hours. Your hotel, airline or car rental company may impose a fee if your booking was made more than 24 hours ago. Look up our Customer Service Portal for more information. Also, be sure to check your itinerary for the nitty-gritty on change fees.
How do I get a cheap travel package to South Loop?
One word: bundle. Flights, hotels and rental cars — combine whatever you need into a South Loop travel package and save. Score even better deals when you add extras such as day tours to your booking. But that's not the only impressive part. You have the flexibility to put together your trip your own way. We offer more than 550 air carriers and 1,000,000 properties across the globe, so that everyone has a chance to travel and fulfil those holiday dreams.
Does Expedia offer Book Now, Pay Later South Loop holidays?
Expedia has joined forces with online lender Klarna to make your next break easier on your hip pocket. Paying by instalment means you can spread the costs of your next big holiday, leaving you with more money to play with while you're away. Klarna has several payment plans to pick from, so you're sure to find one that fits your budget. Browse these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month sounds right for you, Klarna offers just that! Paying in convenient monthly instalments will make that dream getaway possible.
  • Pay in instalments holidays: If you'd prefer to pay for your getaway across multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: Pressing the "book now" button is much easier with this payment plan. Put down a small deposit on your booking and then get on your way.

Where should I stay in South Loop?
Most visitors who travel to South Loop include both Millennium Park and Wrigley Field on their itineraries. Why not go for a hotel that's close to these main attractions?
What are the top hotels in South Loop?
Get your holiday off to a great start by reserving a room at Hyatt Regency Chicago. It's one of most popular hotels in South Loop. Another cosy option is The Godfrey Hotel Chicago.
How far in advance should I book my South Loop holiday?
It's tricky picking the best time for airfares, but we usually say the earlier, the better. Most international journeys on Expedia become available to compare up to 12 months in advance. If you can't book early, don't stress. Discounted prices appear from time to time just weeks before departure dates.
What does an Expedia South Loop travel package include?
With Expedia, you can select any combination of flights, car rentals and hotels to create your ideal South Loop package. Once you've made your booking, you can add on the fun things like sightseeing tours and activities. Remember — the more you bundle, the greater the savings!
What should I know before booking a South Loop travel package?
You'll land amazing savings when you bundle your flights, hotels and rental cars into a package. Not only that, booking everything in one spot makes trip planning much easier. So why waste your money or time? Whether you're organising a luxury city stay with your love or a low-cost family road trip, browse our travel packages today.
Can I choose my airline with a South Loop Expedia travel package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines worldwide. Our packages give you the flexibility to take your pick of available flight, hotel or activity options that suit you.

Stay near popular South Loop attractions

A modern glass building with a curved roof, surrounded by a landscaped garden and a water feature.

McCormick Place

8.8/10 (9,822 reviews)
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

£32
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
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.