South Loop Holidays

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    Save up to €185 when you book a flight and hotel together*
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Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
Price was €898, price is now €706 per person
€706
per person
30 Oct - 2 Nov
found 9 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very Good! (3,812 reviews)
Really liked the close parking, very convenient. Hotel location close to everything downtown. Would stay here again when in Chicago,

Reviewed on 6 Sep 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,559, price is now €1,040 per person
€1,040
per person
30 Oct - 2 Nov
found 9 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Professional service

Reviewed on 4 Sep 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was €1,387, price is now €1,035 per person
€1,035
per person
30 Oct - 2 Nov
found 1 day ago
Return flight included
Shannon (SNN) to Chicago (ORD)
9.4/10 Exceptional! (1,070 reviews)
Great place esp last minute

Reviewed on 5 Sep 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was €1,378, price is now €1,076 per person
€1,076
per person
30 Oct - 2 Nov
found 1 day ago
Return flight included
Shannon (SNN) to Chicago (ORD)
9.2/10 Wonderful! (1,195 reviews)
Beautiful property close to the Fulton Market and night life. The room was eccentric in a way that made our stay cool. It was clean and stocked with a bar & snacks for additional purchase. We enjoyed the Rooftop Cinema on the 6th floor, it was playing my favorite movie! And the restaurant Fora had a delicious breakfast. We definitely recommend this property.

Reviewed on 6 Sep 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was €1,304, price is now €1,021 per person
€1,021
per person
30 Oct - 2 Nov
found 1 day ago
Return flight included
Shannon (SNN) to Chicago (ORD)
9/10 Wonderful! (347 reviews)
Pool area was great

Reviewed on 4 Sep 2025

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 which includes a city

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 €198 per night from 4 Oct to 5 Oct
€198
4 Oct - 5 Oct
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 €209 per night from 25 Sept to 26 Sept
€209
25 Sept - 26 Sept
includes taxes & fees
Hilton Chicago
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 €132 per night from 22 Sept to 23 Sept
€132
22 Sept - 23 Sept
includes taxes & fees
Best Western Grant Park Hotel
See all 4,572 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.

Frequently asked questions

How much does a South Loop holiday package cost?
Starting from a low €706, a holiday package is your passport to low-cost travel. Custom make your South Loop escape by selecting from our extensive range of hotels, flights and rental cars.
How do I get a cheap travel package to South Loop?
Creating your own South Loop holiday package with Expedia is a simple way to save. We have more than 550 airlines and 1,000,000 properties spread across the globe. With such a wonderful range to pick from, you'll have no trouble creating your next dream getaway.
Where should I stay in South Loop?
Make sightseeing a breeze by staying someplace close to South Loop's iconic attractions. McCormick Place and Millennium Park are two of the best in the area.
What are the top hotels in South Loop?
Sonder South Wabash and Hotel BnB are a couple of the most sought-after properties in South Loop. Why not take a look at the rates and facilities at each and then decide?
How far in advance should I book my South Loop holiday?
It can be tricky to know when the best time is to book your trip to South Loop. But generally the earlier you book, the more affordable the prices. In some cases, you can book your flights and hotels up to 12 months before departure. If you're hoping for a last-minute getaway, no need to worry! There are fantastic deals posted on Expedia all the time.
What does an Expedia South Loop travel package include?
That depends on what type of getaway you're thinking about. South Loop holiday deals can include hotels, car rentals and flights. You can mix and match to create the package that fits your needs. You can also add on experiences and activities after you've booked to score even bigger discounts.
What should I know before booking a South Loop travel package?
So many places to wander around, so many things to see and do. With a package, you can check more of them off your list. Combine your hotels, flights and rental cars and see how much you save.
Can I choose my airline with a South Loop Expedia holiday package?
You sure can. Expedia has access to more than 550 partner airlines worldwide, so choose the carrier that's a good fit for your needs.
If I'm not able to travel, can I cancel my South Loop holiday package?
Yes, you can cancel your South Loop booking if your travel plans have been upended. Whether you'll incur a penalty or not depends on your hotel, airline or car rental company. You may be able to change or cancel for free if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.

Things to do

Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

€91
per adult
84% of travellers recommend
Chicago C3® by CityPASS®
Chicago: Field Museum of Natural History Ticket or VIP Tour

Chicago: Field Museum of Natural History Ticket or VIP Tour

€25
per adult
88% of travellers recommend
Chicago: Field Museum of Natural History Ticket or VIP Tour
Chicago's Dark Side Smartphone

Chicago's Dark Side Self-Guided Smartphone Walking Tour

€8
per adult
98% of travellers recommend
Chicago's Dark Side Self-Guided Smartphone Walking Tour
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.