South Loop Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$703 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Your South Loop Holiday

Cafes, bars and pubs and history are just the start of the things waiting for you when you lock in a holiday package to South Loop. Whether you're craving adventure, relaxation or something else, this commercial neighbourhood is likely to have it. Not sure what to see and do during your trip to South Loop? Nearby attractions such as Millennium Park, Willis Tower and Art Institute of Chicago are good places to begin. Expedia will help you turn your ideal South Loop holiday into reality, whatever your budget or travel plans.

Our guide on 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

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

Our pick of the best 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 AU$185 per night from 16 Apr to 17 Apr
AU$185
16 Apr - 17 Apr
includes taxes & fees
8/10 Very Good! (10,032 reviews)
Very clean

Reviewed on 5 Apr 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 AU$381 per night from 10 Apr to 11 Apr
AU$381
10 Apr - 11 Apr
includes taxes & fees
8.6/10 Excellent! (2,723 reviews)
Didn't get the room I reserved (2 months ago), which was 2 double beds. Instead gave me a king (for 2 adults and a child). What's the point of a reservation if they're just going to give my room away? Easter weekend, hotel full of young teenage girls, who instead of acting like young ladies, were ...

Reviewed on 5 Apr 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 AU$214 per night from 26 Apr to 27 Apr
AU$214
26 Apr - 27 Apr
includes taxes & fees
8.8/10 Excellent! (1,947 reviews)
Staff and service was great. I’ve stayed here every year since 2020 and I love it.

Reviewed on 5 Apr 2026

Hilton Garden Inn Chicago Downtown South Loop
See all 4,748 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a South Loop holiday package cost?
Starting from a low , 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.

Discover the most popular places to visit in South Loop

Columbia College Chicago

Walk around the campus at Columbia College Chicago during your visit to Chicago. Discover the fascinating museums and notable monuments in this vibrant area.

Columbia College Chicago

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$38
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$58
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Art Institute of Chicago

Art Institute of Chicago

AU$57
per adult
94% of travellers recommend
Art Institute of Chicago
See all activities in Chicago

Explore a world of travel with Expedia

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