South Loop Vacations

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  • Better together

    Save up to ₩234,741 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

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 showing a city

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

South Loop Hotel Deals

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 ₩128,556 per night from Jan 31 to Feb 1
₩128,556
₩150,912 total
Jan 31 - Feb 1
includes taxes & fees
8/10 Very Good! (9,832 reviews)
Yes perfectly clean

Reviewed on Jan 24, 2026

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 ₩189,206 per night from Feb 2 to Feb 3
₩189,206
₩264,702 total
Feb 2 - Feb 3
includes taxes & fees
8.4/10 Very Good! (2,581 reviews)
My stay was truly amazing. Thank you and appreciate the hotel hospitality

Reviewed on Jan 25, 2026

Hilton Chicago
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
55 E 11th Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₩109,478 per night from Feb 10 to Feb 11
₩109,478
₩128,516 total
Feb 10 - Feb 11
includes taxes & fees
8.8/10 Excellent! (1,829 reviews)
Incredible, helpful front desk staff. Really enjoyed my stay!

Reviewed on Jan 23, 2026

Hilton Garden Inn Chicago Downtown South Loop
See all 4,794 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 , 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 vacation?
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 vacation 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 vacation 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 vacation 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.

Discover the most popular places to visit in South Loop

Navy Pier featuring a sunset and rides

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Beautiful autumn colors surround modern architecture in Millennium Park, Chicago during a sunny day

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Grant Park showing a garden and night scenes

Grant Park

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.