South Loop Holidays from £1,169

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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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £1,484, price is now £1,169 per person
£1,169
per person
13 Jun - 17 Jun
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great and helpful staff very clean, a place where you don’t feel out of place

Reviewed on 25 Apr 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,575, price is now £1,757 per person
£1,757
per person
16 Jun - 23 Jun
found 23 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
Thank you to Javon who was super helpful in our check in . The staff was so nice and accommodating. Additional linens were delivered in less than 5 minutes and then even extended our check out to 1pm. I will definitely be back when I’m in Chicago to try to catch fireworks. Our corner room was outstanding and breathtaking

Reviewed on 3 May 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £3,072, price is now £2,138 per person
£2,138
per person
16 Jun - 23 Jun
found 23 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (1,851 reviews)
The staff was excellent and extremely helpful and informative. The hotel has amazing amenities and location is great!

Reviewed on 3 May 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £2,518, price is now £1,876 per person
£1,876
per person
16 Jun - 23 Jun
found 23 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (1,124 reviews)
Great staff and perfect place to be in the middle of everything!

Reviewed on 27 Apr 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was £3,421, price is now £2,663 per person
£2,663
per person
11 Jul - 18 Jul
found 18 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Breakfasr good, view great

Reviewed on 1 May 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

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 £110 per night from 8 May to 9 May
£110
8 May - 9 May
includes taxes & fees
8/10 Very Good! (10,147 reviews)
.

Reviewed on 4 May 2026

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 £161 per night from 25 May to 26 May
£161
25 May - 26 May
includes taxes & fees
8.6/10 Excellent! (2,774 reviews)
The location was excellent and the staff were helpful. Unfortunately, my room was dirty. There was dust everywhere and the pillow cases on my bed were dirty. I was able to find a housekeeper and she immediately came to give me clean sheets and pillow cases. The WiFi wasn't working which was a bit ...

Reviewed on 4 May 2026

Hilton Chicago
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
55 E 11th Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £115 per night from 26 May to 27 May
£115
26 May - 27 May
includes taxes & fees
8.8/10 Excellent! (1,980 reviews)
Clean room, friendly staff, fast elevator. We would stay here again. Actually, we might prefer to stay at the adjacent hotel run by the same company, (lower room rates and free breakfast are included at that hotel).

Reviewed on 3 May 2026

Hilton Garden Inn Chicago Downtown South Loop
See all 4,681 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
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Beach Holidays
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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 £1,169. 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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
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.