South Loop Holidays

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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.

Price found within the past 48 hours. Click for updated prices.
  • Smart TV
    Jun 24 - Jun 28

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (486 reviews)
    "Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely."
    Reviewed May 22, 2026
    Return • Melbourne (MEL) - Chicago (ORD)
    MEL - ORD • 1 stop ORD - MEL • 1 stop
    AU$4,371
    AU$3,762
    per traveller
    found 2 hours ago
    Level Chicago Fulton Market
  • Terrace/patio
    Jun 24 - Jun 28

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    4 nights
    5.0 star property
    9.6/10 - Exceptional (1,876 reviews)
    "Excellent"
    Reviewed May 21, 2026
    Return • Melbourne (MEL) - Chicago (ORD)
    MEL - ORD • 1 stop ORD - MEL • 1 stop
    AU$5,435
    AU$4,637
    per traveller
    found 2 hours ago
    Trump International Hotel & Tower Chicago
  • Seasonal outdoor pool, pool loungers
    Jun 24 - Jun 28

    Viceroy Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (1,229 reviews)
    "Nice hotel in a great location. "
    Reviewed May 15, 2026
    Return • Melbourne (MEL) - Chicago (ORD)
    MEL - ORD • 1 stop ORD - MEL • 1 stop
    AU$5,114
    AU$4,381
    per traveller
    found 2 hours ago
    Viceroy Chicago
  • 2 restaurants; breakfast, lunch, and dinner served
    Jun 24 - Jun 28

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (3,721 reviews)
    "Great location!"
    Reviewed May 22, 2026
    Return • Melbourne (MEL) - Chicago (ORD)
    MEL - ORD • 1 stop ORD - MEL • 1 stop
    AU$4,627
    AU$3,997
    per traveller
    found 2 hours ago
    LondonHouse Chicago, Curio Collection by Hilton
  • Meeting facility
    Jun 24 - Jun 28

    Thompson Chicago, by Hyatt + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.2/10 - Wonderful (1,366 reviews)
    "Great location"
    Reviewed May 19, 2026
    Return • Melbourne (MEL) - Chicago (ORD)
    MEL - ORD • 1 stop ORD - MEL • 1 stop
    AU$4,788
    AU$4,193
    per traveller
    found 2 hours ago
    Thompson Chicago, by Hyatt

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$222 per night from 25 May to 26 May
AU$222
25 May - 26 May
includes taxes & fees
8/10 Very Good! (10,130 reviews)
"As one of my first solo trips, I was glad to feel very safe and comfortable during my stay. I had requested and paid extra for a lake front room. On the fourth floor I could barely see the lake, but did face the park. Good news and bad news because the street noise was very loud at times. I ate in ..."

Reviewed on 22 May 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$373 per night from 25 May to 26 May
AU$373
25 May - 26 May
includes taxes & fees
8.6/10 Excellent! (2,808 reviews)
"We stayed 5 nights. Our looked out on beautiful Lake Michigan. We had an adjoining rooms which we could hear everything in the next room. The reason for a 3 star rating is we were there 5 nights. Our room was only cleaned 2 times. So on the days there was no room cleaning, when we got back at night ..."

Reviewed on 22 May 2026

Hilton Chicago
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
The price is AU$373 per night from 24 May to 25 May
AU$373
24 May - 25 May
includes taxes & fees
9.2/10 Wonderful! (1,074 reviews)
"Very quiet and clean and very big gym"

Reviewed on 14 May 2026

Hyatt Regency McCormick Place Chicago
See all 4,677 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
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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 acclaimed art galleries and notable monuments in this vibrant area.

Columbia College Chicago

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

AU$61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

AU$55
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Chicago

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