South Loop Holidays

Book a Hotel + Flight or Car together to unlock savings

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

5 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Top hotels in South Loop

Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is 3.001.435 ₫ per night from 29 Dec to 30 Dec
3.001.435 ₫
4.296.260 ₫ total
29 Dec - 30 Dec
includes taxes & fees
8.4/10 Very Good! (2,410 reviews)
Staff very friendly

Reviewed on 22 Dec 2025

Hilton Chicago
Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

3 out of 5
59 E. 11th Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is 2.136.252 ₫ per night from 13 Jan to 14 Jan
2.136.252 ₫
2.507.747 ₫ total
13 Jan - 14 Jan 2026
includes taxes & fees
8.6/10 Excellent! (2,148 reviews)
Yes

Reviewed on 21 Dec 2025

Homewood Suites by Hilton Chicago Downtown 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 5.423.522 ₫ per night from 31 Dec to 1 Jan
5.423.522 ₫
6.366.673 ₫ total
31 Dec - 1 Jan 2026
includes taxes & fees
8/10 Very Good! (9,690 reviews)
Was good, clean… not haunted just old… but renovated and up to date… I paid an up charge for the lake view. Fairly priced up charge for the difference in view. Staff was friendly.

Reviewed on 22 Dec 2025

Congress Plaza Hotel
See all 4,748 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 , 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 1null000null000 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.

Popular places to visit

McCormick Place

McCormick Place

During your trip, find out what's happening in McCormick Place, a top convention centre in Chicago. Discover the acclaimed theatre scene and notable monuments in this vibrant area.

McCormick Place
Soldier Field which includes a high-rise building, a city and modern architecture

Soldier Field

Catch an event at Soldier Field during your trip to Chicago. Stroll along the lakeside or visit the notable monuments in this vibrant area.

Soldier Field
Adler Planetarium and Astronomy Museum featuring modern architecture

Adler Planetarium and Astronomy Museum

You can spend an afternoon studying the exhibits at Adler Planetarium and Astronomy Museum during your travels in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

Adler Planetarium and Astronomy Museum