South Loop Holidays from NZ$2,395

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Top Holiday Package Deals in South Loop

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was NZ$2,901, price is now NZ$2,395 per person
NZ$2,395
per person
21 Jan - 26 Jan
found 1 day ago
Return flight included
Wellington (WLG) to Chicago (ORD)
9.4/10 Exceptional! (2,229 reviews)
It was seamless. That was how it should! ❤️

Reviewed on 21 Dec 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was NZ$4,972, price is now NZ$3,868 per person
NZ$3,868
per person
21 Jan - 26 Jan
found 1 day ago
Return flight included
Wellington (WLG) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Best hotel in Chicago

Reviewed on 21 Dec 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was NZ$3,112, price is now NZ$2,499 per person
NZ$2,499
per person
21 Jan - 26 Jan
found 1 day ago
Return flight included
Wellington (WLG) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Overall good experience. My room was not cleaned one of the nights because the maid didn’t come until late but we were already in our room. Also, the $25/night resort fee was not properly explained to me, didn’t make much sense at all honestly. Property is nice and in a great location but i wouldn’t stay here again

Reviewed on 19 Dec 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was NZ$3,198, price is now NZ$2,579 per person
NZ$2,579
per person
21 Jan - 26 Jan
found 1 day ago
Return flight included
Wellington (WLG) to Chicago (ORD)
9.2/10 Wonderful! (326 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.

Reviewed on 18 Dec 2025

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Price was NZ$3,037, price is now NZ$2,511 per person
NZ$2,511
per person
21 Jan - 26 Jan
found 1 day ago
Return flight included
Wellington (WLG) to Chicago (ORD)
8.4/10 Very Good! (2,301 reviews)
Room temperature control on th 6th floor was terrible. Way too hot even when turning temp down as low as it would go. Had to open windows to sleep. In the morning went to grab 2 coffees for over $20 and $80 for parking on top of room. Absolute rip off. Room was definitely getting dated, pillows, bed and sheets were cheap. Definitely not what I would expectbfrom the Hilton. On a positive, staff was very nice.

Reviewed on 21 Dec 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

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

Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$283 per night from 28 Dec to 29 Dec
NZ$283
28 Dec - 29 Dec
includes taxes & fees
8.4/10 Very Good! (2,400 reviews)
So friendly and our room was spotless

Reviewed on 21 Dec 2025

Hilton Chicago
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$420 per night from 31 Dec to 1 Jan
NZ$420
31 Dec - 1 Jan 2026
includes taxes & fees
8/10 Very Good! (9,668 reviews)
The breakfast menu was good but I was staying all week and I felt a little entrapped to pay for full breakfasts every morning since I stay there the year prior and there was plenty of complimentary items at the buffet that was included to fill me up. The free breakfast item options were pretty thin. ...

Reviewed on 18 Dec 2025

Congress Plaza Hotel
Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

3 out of 5
59 E. 11th Street Chicago IL
The price is NZ$166 per night from 5 Jan to 6 Jan
NZ$166
5 Jan - 6 Jan 2026
includes taxes & fees
8.6/10 Excellent! (2,146 reviews)
This was our first visit to Chicago. The room was clean and large for the 2 of us. Very inviting. Location was close to 2 major bus routes that took us every where we wanted to go.

Reviewed on 19 Dec 2025

Homewood Suites by Hilton 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.

Frequently asked questions

How much does a South Loop holiday package cost?
Starting from a low NZ$2,395, 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
Field Museum of Natural History showing a city

Field Museum of Natural History

4.5/5(9 reviews)

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

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

Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

NZ$70
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Lineup with Capone and Dillinger!

Chicago Crime and Mob Bus Tour

NZ$76
per adult
92% of travellers recommend
Chicago Crime and Mob Bus Tour
Art Institute of Chicago

Art Institute of Chicago

NZ$69
per adult
92% of travellers recommend
Art Institute of Chicago
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.