South Loop Holidays

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

The Chicago Hotel Collection River North

3 out of 5
Downtown Chicago
per person
31 May - 2 Jun
found 3 hours ago
Return direct flight included
Toronto (YTO) to Chicago (ORD)
7.2/10 Good! (434 reviews)
The decor is really nice and the rooms / beds are incredibly comfortable. A little bit smaller than I expected but still a great place to stay.

Reviewed on 18 Apr 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
31 May - 2 Jun
found 3 hours ago
Return direct flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (295 reviews)
Front desk was very friendly and helpful. We had a corner unit and the view was great. The unit was very comfortable and clean.

Reviewed on 22 Apr 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
31 May - 2 Jun
found 3 hours ago
Return direct flight included
Toronto (YTO) to Chicago (ORD)
8/10 Very Good! (1,524 reviews)
The only thing that we didn’t like was the fact that we got a parking ticket in front of the valet sign when we was told that it was saved to park there by the valet attendant

Reviewed on 24 Apr 2025

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
31 May - 2 Jun
found 3 hours ago
Return direct flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (380 reviews)
it was as it advertising. clean, tourist friendly

Reviewed on 13 Apr 2025

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
31 May - 2 Jun
found 3 hours ago
Return direct flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,929 reviews)
Very well located. Clean and very nice room. Love the shower

Reviewed on 26 Apr 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 HK$1,111 per night from 2 May to 3 May
HK$1,111
HK$1,305 total
includes taxes & fees
2 May - 3 May
7.8/10 Good! (8,694 reviews)
"I enjoyed everything"

Reviewed on 23 Apr 2025

Congress Plaza Hotel
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 HK$758 per night from 26 May to 27 May
HK$758
HK$890 total
includes taxes & fees
26 May - 27 May
8/10 Very Good! (2,510 reviews)
"Great location. Shower flooded to other areas in restroom despite shower cover"

Reviewed on 24 Apr 2025

Best Western Grant Park 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 HK$1,358 per night from 2 May to 3 May
HK$1,358
HK$1,822 total
includes taxes & fees
2 May - 3 May
8.2/10 Very Good! (1,801 reviews)
"The bar was so crowded they needed 3 more bartenders"

Reviewed on 25 Apr 2025

Hilton Chicago
See all 4,195 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 vacation package cost?
Starting from a low HK$3,519, a vacation 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 vacation 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

Soldier Field featuring modern architecture, a city and a high-rise building

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
Ping Tom Memorial Park

Ping Tom Memorial Park

After visiting Ping Tom Memorial Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

Ping Tom Memorial Park

Wintrust Arena

3.5/5(2 reviews)

Catch an event at Wintrust Arena during your trip to Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.

Wintrust Arena

Things to do

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

Chicago C3® by CityPASS®

HK$824
per adult
86% of travellers recommend
Chicago C3® by CityPASS®
Chicago's Dark Side Smartphone

Chicago's Dark Side Self-Guided Smartphone Walking Tour

HK$76
per adult
98% of travellers recommend
Chicago's Dark Side Self-Guided Smartphone Walking Tour
Field Museum of Natural History All-Access Pass

Field Museum of Natural History All-Access Pass

HK$319
per adult
Field Museum of Natural History All-Access Pass
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.