South Loop Holidays from £851
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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.
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Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
£1,475
per person
26 Oct - 31 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,681 reviews)
Be aware of all the hidden changes and you have to ask for housing keeping to clean your room. Stayed 6 days and didn’t get my room cleaned once. No fresh towels, no clean water, and no maid beds. When we brought it up to learn about charges that were made they told us that we should have asked for house keeping to brings towels, etc.
Reviewed on 16 Sept 2026
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
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.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
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.
Top hotels in South Loop
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£155
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
Travelodge by Wyndham Downtown Chicago
65 E Harrison St Chicago IL
Fully refundableReserve now, pay when you stay
£137
27 Sept - 28 Sept
includes taxes & fees
7.8/10 Good! (2,836 reviews)
"Hotel located in a great area that you can walk to many places or access public transportation easily. For an older building, it is well kept and clean and friendly staff. Only thing is the room was a bit basic with no refrigerator & microwave but those are accessible on the 12th floor."
Reviewed on 17 Sept 2026
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
How much does a South Loop travel package cost?
Chart your own course with our South Loop travel packages, which start from just £851. 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
Photo by © City of Chicago
Soldier Field
8.8/10 (7,063 reviews)
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Photo by © Cesar Russ Photography
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.
Photo by City Of Chicago
Field Museum of Natural History
9.4/10 (1,744 reviews)
Dinosaur bones, rare gems and real Egyptian mummies are among the displays at this family favorite.
Adler Planetarium and Astronomy Museum
8.8/10 (248 reviews)
Opportunities for fun, learning and wonder abound at this historic and state-of-the-art museum on the pretty shore of Lake Michigan.
Northerly Island Natural Area
8.6/10 (28 reviews)
Bird life, paved paths and a built-in music venue give one of Chicago’s newest green spaces much to offer to nature lovers, exercisers and music fans.
Wintrust Arena
8.0/10 (70 reviews)
Catch an event at Wintrust Arena during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.
Columbia College Chicago
8.4/10 (164 reviews)
Walk around the campus at Columbia College Chicago during your visit to Chicago. Discover the fascinating museums and notable monuments in this vibrant area.
Arie Crown Theater
8.0/10 (9 reviews)
You can get tickets for a performance at Arie Crown Theater during your stay in Chicago. Experience the fascinating museums and acclaimed art galleries 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
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- Flights to Chicago
- American Airlines Dublin (DUB) to Chicago (ORD) flights
- Flights from Chicago
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- Art Institute of Chicago
- Blue Island Holidays
- Visit Downtown Chicago
- Chicago Harbor Lighthouse
- Visit Magnificent Mile
- Visit Near South Side
- Visit Prairie District
- Visit Printers Row
- Chicago Riverwalk
- Visit South Loop
- 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
- 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
- The Loop Holidays
- 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.