Near South Side Holidays from NZ$2,045

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Top Holiday Package Deals in Near South Side

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was NZ$2,596, price is now NZ$2,045 per person
NZ$2,045
per person
4 Nov - 9 Nov
found 1 day ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.2/10 Wonderful! (2,120 reviews)
The hotel staff was great from the door men to front desk staff everyone was great.

Reviewed on 23 Sept 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was NZ$4,661, price is now NZ$3,143 per person
NZ$3,143
per person
4 Nov - 9 Nov
found 1 day ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Worth every penny! Not much more than the "average" hotel when comparing all of the amenities. Will definitely stay here again!

Reviewed on 23 Sept 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was NZ$2,946, price is now NZ$2,122 per person
NZ$2,122
per person
4 Nov - 9 Nov
found 1 day ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The room was perfect and the front staff were exceptional. Our stay was amazing!

Reviewed on 21 Sept 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was NZ$3,179, price is now NZ$2,500 per person
NZ$2,500
per person
4 Nov - 9 Nov
found 1 day ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.4/10 Exceptional! (3,344 reviews)
Close to the riverwalk

Reviewed on 23 Sept 2025

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$2,963, price is now NZ$2,347 per person
NZ$2,347
per person
4 Nov - 9 Nov
found 1 day ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.4/10 Exceptional! (2,142 reviews)
Great view and a great staff!

Reviewed on 22 Sept 2025

Our guide on where to stay in Near South Side

Find the best Near South Side areas and neighborhoods for the activities you enjoy most. Learn more about Near South Side
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 Near South Side 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
7.8/10 Good! (9,228 reviews)
"Hotel is older, but very well maintained."

Reviewed on 19 Sept 2025

Get rates
Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$322 per night from 20 Oct to 21 Oct
NZ$322
20 Oct - 21 Oct
includes taxes & fees
8.8/10 Excellent! (2,901 reviews)
"Great location, close to different restaurants and coffee shops. Sadly the pool was closed when I was there but it looked like the property was very well maintained. Staff was so nice upon check in. Our room was nice and comfortable! Enjoyed my stay and will be back!!"

Reviewed on 19 Sept 2025

Hilton Chicago/Magnificent Mile Suites
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
The price is NZ$361 per night from 2 Oct to 3 Oct
NZ$361
2 Oct - 3 Oct
includes taxes & fees
8.4/10 Very Good! (3,934 reviews)
"It was walking distance to Michigan Ave"

Reviewed on 21 Sept 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 4,500 properties in Near South Side
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 Near South Side holiday package cost?
The most affordable Near South Side package is NZ$2,045, so your dream holiday can become a reality — without a hefty price tag. Bundle flights, hotels, car rentals and more to custom build a package that suits your travel style.
How do I get a cheap travel package to Near South Side?
Our Near South Side holiday packages mean plenty of savings for the savvy traveller. For the best deal, simply bundle your hotel, flights and extras (such as activities) into a budget-friendly package. But cheap prices are only the start of your next big adventure. Book with Expedia and you'll have more than 550 airlines and 1 000 000 hotels all over the world to choose from. Whatever your style or budget, there's a package here just for you.
Where should I stay in Near South Side?
Most who travel to Near South Side put both McCormick Place and Millennium Park on their to-do lists. Why not select a hotel within walking distance of these great attractions?
What are the top hotels in Near South Side?
If it's your first visit to Near South Side, lock in a room at Sonder South Wabash or Hotel BnB. Both hotels will make you feel at home and are favourites among many travellers.
How far in advance should I book my Near South Side holiday?
It all depends on the airline, but you can normally compare international flights on Expedia up to 12 months in advance. While it's generally recommended to book ahead of time, lucky customers occasionally nab a cheaper flight just weeks prior to their intended journey.
What does an Expedia Near South Side travel package include?
Choose from a combination of flights, hotels and rental cars. Once you've made your booking, you can add some experiences and tours. Want to pick your fare class? That's easily done too. The choice is yours when it comes to crafting your dream Near South Side escape.
What should I know before booking a Near South Side travel package?
Tailor deals that suit your budget with an Expedia package. Flights, hotels, rental cars — we've got everything you need to plan your getaway. You'll save big bucks just by bundling your bookings. Whether you're embarking on a winter adventure or sunning yourself on a warm beach, your ideal getaway is only a few clicks away.
Can I choose my airline with a Near South Side Expedia holiday package?
Yes, the choice is yours. We offer more than 550 partner airlines globally, so you can tailor your Near South Side escape according to your budget and style.
If I'm not able to travel, can I cancel my Near South Side holiday package?
We totally get it — life can throw you the odd curveball. If you've booked a Near South Side holiday package and need to cancel or change it, we can help. It's always worth checking out our Customer Service Portal first for information. But generally, if you've booked your package in the last 24 hours, you may be able to change your itinerary for free. If it's more than 24 hours, your hotel, airline or car rental company may impose a fee.

Discover the most popular places to visit in Near South Side

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

Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

NZ$180
per adult
82% of travellers recommend
Chicago C3® by CityPASS®
Chicago: Field Museum of Natural History Ticket or VIP Tour

Chicago: Field Museum of Natural History Ticket or VIP Tour

NZ$49
per adult
88% of travellers recommend
Chicago: Field Museum of Natural History Ticket or VIP Tour
Field Museum of Natural History Ticket with Self-Guided Audio Tour

Field Museum of Natural History Ticket with Self-Guided Audio Tour

NZ$107
per adult
100% of travellers recommend
Field Museum of Natural History Ticket with Self-Guided Audio 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.