South Loop Holidays from AU$1,890

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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.

Top Holiday Package Deals in South Loop

Price found within the past 48 hours. Click for updated prices.
21c Museum Hotel Chicago

21c Museum Hotel Chicago

4 out of 5
Downtown Chicago
per person
30 Jan - 2 Feb
found 22 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
8.6/10 Excellent! (1,923 reviews)
Hotel is centrally located and convenient, don’t believe our room was fully cleaned though, found an old food container on the ground.

Reviewed on 2 Dec. 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
30 Jan - 2 Feb
found 22 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (1,484 reviews)
Loved the room I was in.

Reviewed on 3 Dec. 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
30 Jan - 2 Feb
found 22 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (931 reviews)
Great customer service great and convenient location. Only gave 4 stars cause carpet looks dirty and chandelier had dust and spider Web and room was too warm.

Reviewed on 30 Nov. 2024

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
30 Jan - 2 Feb
found 22 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (1,239 reviews)
Early check in, staff more than helpful, room was comfortable and clean, will stay again.

Reviewed on 30 Nov. 2024

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
30 Jan - 2 Feb
found 22 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.6/10 Exceptional! (1,005 reviews)
Excellent everything

Reviewed on 24 Nov. 2024

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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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 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 Millennium Park are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotel + flight trips 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$189 per night from 16 Dec to 17 Dec
AU$189
includes taxes & fees
16 Dec - 17 Dec
7.8/10 Good! (8,177 reviews)
"We stay here every year for the hot chocolate run and it’s so convenient!"

Reviewed on 3 Dec. 2024

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 AU$129 per night from 16 Dec to 17 Dec
AU$129
includes taxes & fees
16 Dec - 17 Dec
8/10 Very Good! (2,540 reviews)
"A bit noisy but close nice walkable location. Staff? As friendly and courteous. The hot water is very touchy so be careful!"

Reviewed on 1 Dec. 2024

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 AU$261 per night from 22 Dec to 23 Dec
AU$261
includes taxes & fees
22 Dec - 23 Dec
8.2/10 Very Good! (1,481 reviews)
"We had a great time in Chicago - what a beautiful city!"

Reviewed on 1 Dec. 2024

Hilton Chicago
See all 4,141 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 AU$1,890, 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

McCormick Place

McCormick Place

4.5/5(21 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
Soldier Field featuring a city, modern architecture and a high-rise building

Soldier Field

4/5(13 reviews)

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Soldier Field
Adler Planetarium and Astronomy Museum featuring modern architecture

Adler Planetarium and Astronomy Museum

4/5(1 review)

Opportunities for fun, learning and wonder abound at this historic and state-of-the-art museum on the pretty shore of Lake Michigan.

Adler Planetarium and Astronomy Museum

Activities

Go City - Chicago All-Inclusive Pass: 1 to 5 Day Access to 25+ Activities

Chicago Pass: Save up to 50 Percent - Includes 360 Chicago

AU$200
Per adult
78% of travellers recommend
Chicago Pass: Save up to 50 Percent - Includes 360 Chicago
Chicago's Dark Side Smartphone

Chicago's Dark Side Self-Guided Smartphone Walking Tour

AU$11
Per adult
100% 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

AU$63
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.