South Loop Holidays from £1,309

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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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
15 Jul - 22 Jul
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (703 reviews)
The location of the hotel was very convenient to shopping, parks, restaurants, museums, etc. The bed was really comfortable. The bathroom was nice, but the lighting was really dim. The lighting in the hallways on our floor was really dim as well. There were coffee and apples available in the lobby in the morning, but no bananas as indicated on the sign. Also, the coffee was gone one morning by 9:30 am. It seems like coffee should at least be available to guests most of the day for the price of the rooms. We were also disappointed that the rooftop bar was closed, even though it indicated online that it would be open over Memorial Day weekend.

Reviewed on 6 Jun 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
15 Jul - 22 Jul
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,212 reviews)
Property is 5 star all the way. Staff is excellent. Restaurant is 5 star as well.

Reviewed on 6 Jun 2024

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
15 Jul - 22 Jul
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
Very friendly and helpfu

Reviewed on 31 May 2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
15 Jul - 22 Jul
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (3,522 reviews)
Loved the central location. Major sites in walking distance. All the staff were extremely friendly.

Reviewed on 6 Jun 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
15 Jul - 22 Jul
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.8/10 Excellent! (208 reviews)
The staff here is amazing and so helpful. Loved my stay here.

Reviewed on 6 Jun 2024

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 featuring a city

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

Best Western Grant Park Hotel
Best Western Grant Park Hotel
2.5 out of 5
1100 S Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £106 per night from 1 Jul to 2 Jul
£106
per night
1 Jul - 2 Jul
7.8/10 Good! (2,533 reviews)
"Location was perfect , pricing was great"

Reviewed on 2 Jun 2024

Best Western Grant Park Hotel
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 £136 per night from 16 Jun to 17 Jun
£136
per night
16 Jun - 17 Jun
7.6/10 Good! (6,849 reviews)
"Great location, historic feel. Pleasant stay"

Reviewed on 4 Jun 2024

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 £112 per night from 1 Jul to 2 Jul
£112
per night
1 Jul - 2 Jul
6.4/10 (1,697 reviews)
"Classic hotel just what i expected for price and excellent location close to Millennium and Grant Park."

Reviewed on 5 Jun 2024

Travelodge by Wyndham Downtown Chicago
See all 4,145 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 £1,309. 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.

Popular places to visit

Image for McCormick Place

McCormick Place

4.5/5(36 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.

McCormick Place
Image for Soldier Field

Soldier Field

4/5(44 reviews)

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Soldier Field
Image for Shedd Aquarium

Shedd Aquarium

4.5/5(29 reviews)

Make time in your itinerary to visit the sea life who live at Shedd Aquarium during your visit to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

Shedd Aquarium

Things to do

Image for Chicago C3® by CityPASS®

Chicago C3® by CityPASS®

£81
Per adult
78% of travellers recommend
Chicago C3® by CityPASS®
Image for Chicago's Dark Side Self-Guided Smartphone Walking Tour

Chicago's Dark Side Self-Guided Smartphone Walking Tour

£6
Per adult
100% of travellers recommend
Chicago's Dark Side Self-Guided Smartphone Walking Tour
Image for Field Museum of Natural History Ticket with Self-Guided Audio Tour

Field Museum of Natural History Ticket with Self-Guided Audio Tour

£38
Per adult
100% of travellers recommend
Field Museum of Natural History Ticket with Self-Guided Audio Tour
See all activities in Chicago

More trip options

* 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.