South Loop Holidays

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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
per person
15 May - 20 May
found 20 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8/10 Very Good! (1,524 reviews)
Love booking a room there

Reviewed on 23 Mar 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
15 May - 20 May
found 20 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,310 reviews)
Great stay on St. Patrick's Day weekend.

Reviewed on 24 Mar 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
15 May - 20 May
found 20 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,046 reviews)
The Emily Hotel is a phenomenal place. Leo at the front desk was amazing at checking us in and making our experience so much better. Great stay!! And we look forward to going back for rooftop movie nights!!!

Reviewed on 23 Mar 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
15 May - 20 May
found 20 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,546 reviews)
Excellent, just what anyone would expect from this brand.

Reviewed on 25 Mar 2025

Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
per person
15 May - 20 May
found 20 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,608 reviews)
The staff was great, it was nice they have a free cocktail bar at night where you get two adult beverages everyday. The breakfast was decent for a free breakfast. the bad, the hotel was under construction which was not communicated at time of booking. Only one elevator was operational so the wait times were long every time. The walls in the hotel were paper thin. The room next to us was empty but we could hear the kids two rooms down our entire stay. Pictures online show a walk in shower, not what our room had, and the beds were not comfortable.

Reviewed on 24 Mar 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 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

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 €117 per night from 2 Apr to 3 Apr
€117
includes taxes & fees
2 Apr - 3 Apr
7.8/10 Good! (8,626 reviews)
"I was running a race that started and ended in grant park. This was a perfect location to get there and back after, and the late check out was a bonus"

Reviewed on 24 Mar 2025

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 €198 per night from 6 Apr to 7 Apr
€198
includes taxes & fees
6 Apr - 7 Apr
8.2/10 Very Good! (1,732 reviews)
"Cool"

Reviewed on 25 Mar 2025

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 €88 per night from 7 Apr to 8 Apr
€88
includes taxes & fees
7 Apr - 8 Apr
8/10 Very Good! (2,432 reviews)
"Staff were great but the elevators sounded like they could breakdown any minute and the hallways were very noisy. Rooms not very clean. Have stayed multiple times in this same hotel due to location to the Museum district and standards have lowered for sure."

Reviewed on 24 Mar 2025

Best Western Grant Park Hotel
See all 4,187 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 €1,274, 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.

Popular places to visit

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
Soldier Field which includes a city, modern architecture and a skyscraper

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
Field Museum of Natural History which includes a city

Field Museum of Natural History

4.5/5(27 reviews)

Dinosaur bones, rare gems and real Egyptian mummies are among the displays at this family favorite.

Field Museum of Natural History

Things to do

Chicago: Field Museum of Natural History Ticket or VIP Tour

Chicago: Field Museum of Natural History Ticket or VIP Tour

€27
per adult
86% of travellers recommend
Chicago: Field Museum of Natural History Ticket or VIP Tour
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

€98
per adult
86% of travellers recommend
Chicago C3® by CityPASS®
Chicago's Dark Side Smartphone

Chicago's Dark Side Self-Guided Smartphone Walking Tour

€6
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.