South Loop Holidays

    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to €150 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

3 out of 5
Downtown Chicago
per person
8 Nov - 11 Nov
found 23 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (1,138 reviews)
great place to stay to see the city will definitely come back again

Reviewed on 30 Sep 2024

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
per person
8 Nov - 11 Nov
found 22 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (1,317 reviews)
The location is great, right on the river. The rooms are a bit outdated. The staff wasn’t as friendly as I’m used to for a 4 star hotel. They also charge a daily fee. It can be used for room service but everything is pretty pricey and there’s a $5 delivery fee which I didn’t notice until after ordering.

Reviewed on 24 Sep 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
8 Nov - 11 Nov
found 22 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (257 reviews)
Amenities are excellent.

Reviewed on 26 Sep 2024

W Chicago - Lakeshore

W Chicago - Lakeshore

4.5 out of 5
Downtown Chicago
per person
8 Nov - 11 Nov
found 22 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (1,007 reviews)
Just micro oven was lacked in the room

Reviewed on 25 Sep 2024

Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
per person
8 Nov - 11 Nov
found 22 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (998 reviews)
Checking in and out was a breeze and the hotel staff was amazing

Reviewed on 29 Sep 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

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

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 €123 per night from 27 Oct to 28 Oct
€123
per night
27 Oct - 28 Oct
6.6/10 (1,965 reviews)
"While the property was certainly on the older side, it was clean and well taken care of. The staff was attentive. The location is fantastic. Unlike some other places on the affordable side, this one was quiet and I couldn’t hear any of my neighbors which, turns out, I immensely appreciated. Definitely ..."

Reviewed on 27 Sep 2024

Travelodge by Wyndham Downtown Chicago
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 €143 per night from 1 Oct to 2 Oct
€143
per night
1 Oct - 2 Oct
7.6/10 Good! (7,926 reviews)
"The hotel is very old and the room perhaps needed a little more maintenance. The dining room for breakfast could have been a little more inviting and perhaps a little more healthy choices. The Bellman, Marco, was very helpful as well as maintenance. My door was difficult to open and someone was sent ..."

Reviewed on 29 Sep 2024

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 €221 per night from 27 Oct to 28 Oct
€221
per night
27 Oct - 28 Oct
8.2/10 Very Good! (1,355 reviews)
"Leslie is AWESOME! She has the best personality to work in hospitality, and SHE is what made our stay great! Give that girl a raise!"

Reviewed on 27 Sep 2024

Hilton Chicago
See all 3,854 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 €646, 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

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 theatre scene.

Shedd Aquarium

Things to do

Image for Go City - Chicago All-Inclusive Pass: 1 to 5 Day Access to 30+ Activities

Go City - Chicago All-Inclusive Pass: 1 to 5 Day Access to 30+ Activities

€117
Per adult
78% of travellers recommend
Go City - Chicago All-Inclusive Pass: 1 to 5 Day Access to 30+ Activities
Image for Chicago: Field Museum of Natural History Ticket or VIP Tour

Chicago: Field Museum of Natural History Ticket or VIP Tour

€26
Per adult
84% of travellers recommend
Chicago: Field Museum of Natural History Ticket or VIP Tour
Image for Chicago C3® by CityPASS®

Chicago C3® by CityPASS®

€92
Per adult
82% 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.