South Loop Holidays from NZ$2,542

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Top Holiday Package Deals in South Loop

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
per person
15 Aug - 18 Aug
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
8.4/10 Very Good! (3,410 reviews)
It was a convenient location and very clean. Would be nice if they offered a small breakfast for free.

Reviewed on 21 Jun. 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
15 Aug - 18 Aug
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,613 reviews)
Great hotel with great staff.

Reviewed on 20 Jun. 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
15 Aug - 18 Aug
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (2,039 reviews)
The consistency of excellence is what RIU does so well. This is our third stay at a RIU HOTEL. We are definitely planning for our fourth. From entering to exit, it was a wonderful and easygoing experience.

Reviewed on 22 Jun. 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
15 Aug - 18 Aug
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (319 reviews)
I had no idea how nice this property would be! I had a full one-bedroom apartment and amazing view and amenities. 10/10, would stay again!

Reviewed on 1 Jun. 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
15 Aug - 18 Aug
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,087 reviews)
Great setup, location

Reviewed on 21 Jun. 2025

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 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

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 NZ$281 per night from 3 July to 4 July
NZ$281
3 July - 4 July
includes taxes & fees
7.8/10 Good! (8,858 reviews)
"The room air conditioning did not cool the room and the lighting for the restroom was poor , hard to do makeup."

Reviewed on 20 Jun. 2025

Congress Plaza Hotel
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago
2 out of 5
65 E Harrison St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$182 per night from 7 July to 8 July
NZ$182
7 July - 8 July
includes taxes & fees
7/10 Good! (2,206 reviews)
"Good hotel."

Reviewed on 19 Jun. 2025

Travelodge by Wyndham Downtown Chicago
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 NZ$226 per night from 30 June to 1 July
NZ$226
30 June - 1 July
includes taxes & fees
8/10 Very Good! (2,521 reviews)
"Good location and served out purpose. The elevators were a little on the slow side but other than that really convenient in location. They have coffee in the lobby which is very important lol!"

Reviewed on 19 Jun. 2025

Best Western Grant Park Hotel
See all 4,489 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 holiday package cost?
Starting from a low NZ$2,542, 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

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
Field Museum of Natural History showing a city

Field Museum of Natural History

Explore hidden worlds, ancient secrets, and bizarre creatures – and a dinosaur terror named Sue.

Field Museum of Natural History
Adler Planetarium and Astronomy Museum featuring modern architecture

Adler Planetarium and Astronomy Museum

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

Chicago: Field Museum of Natural History Ticket or VIP Tour

Chicago: Field Museum of Natural History Ticket or VIP Tour

NZ$48
per adult
88% of travellers recommend
Chicago: Field Museum of Natural History Ticket or VIP Tour
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

NZ$175
per adult
88% of travellers recommend
Chicago C3® by CityPASS®
Chicago's Dark Side Smartphone

Chicago's Dark Side Self-Guided Smartphone Walking Tour

NZ$16
per adult
98% of travellers recommend
Chicago's Dark Side Self-Guided Smartphone Walking Tour
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.