South Loop Holidays from £945

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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.
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 South Loop

Find the best South Loop areas and neighborhoods for the activities you enjoy most. Learn more about South 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 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 £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
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is £197 per night from 5 Jul to 6 Jul
£197
5 Jul - 6 Jul
includes taxes & fees
8.6/10 Excellent! (2,869 reviews)
"Gave us an upgrade at checkin that meant a lot :) Also halpily gave me ibuprofen at 3:00 a.m! Lovely property in a nice location by the lake!"

Reviewed on 18 Jun 2026

Hilton Chicago
See all 4,591 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.
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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 £945. 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
Open Photo by © City of Chicago

Soldier Field

8.8/5 (7,063 reviews)
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
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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.