South Loop Holidays

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Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
3 Apr - 9 Apr
found 23 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,550 reviews)
I liked it for the most part just a little busy at night

Reviewed on 24 Feb 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
3 Apr - 9 Apr
found 23 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (287 reviews)
Amazing stay ! Love this property every time I’m in Chicago.

Reviewed on 20 Jan 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
3 Apr - 9 Apr
found 23 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (998 reviews)
Clean, modern, staff provided excellent and friendly service. The hotel was centrally located in a great area with shopping and dining options. Beautiful decor and comfy rooms.

Reviewed on 24 Feb 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
3 Apr - 9 Apr
found 23 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,279 reviews)
Very good place to stay

Reviewed on 24 Feb 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
per person
3 Apr - 9 Apr
found 23 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
I was upset that the elevators were not working and it took a long to get to my room and the lobby. I would have appreciated communication about this ahead of time and would have switched hotels. Apparently it had been an issue for at least two weeks. The staff were amazing. The rooms were dark and small.

Reviewed on 14 Feb 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

4 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 €96 per night from 25 Feb to 26 Feb
€96
includes taxes & fees
25 Feb - 26 Feb
7.8/10 Good! (8,525 reviews)
"Just a easy place to stay at"

Reviewed on 21 Feb 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 €205 per night from 3 Mar to 4 Mar
€205
includes taxes & fees
3 Mar - 4 Mar
8.2/10 Very Good! (1,666 reviews)
"Arrived early and room wasn't ready but was given a room number and told that if we were assigned a new room that that number would be texted to me. Never received text about room change, when my party returned to hotel late Friday we were unable to find the room and when I inquired at front desk ..."

Reviewed on 24 Feb 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 €78 per night from 9 Mar to 10 Mar
€78
includes taxes & fees
9 Mar - 10 Mar
8/10 Very Good! (2,497 reviews)
"."

Reviewed on 21 Feb 2025

Best Western Grant Park Hotel
See all 4,262 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 €823, 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

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

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

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

€28
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®

€99
per adult
84% of travellers recommend
Chicago C3® by CityPASS®
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.