Near South Side Holidays

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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

Top hotels in Near South Side

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 Rp1.496.221 per night from 14 Jan to 15 Jan
Rp1.496.221
Rp1.756.413 total
14 Jan - 15 Jan
includes taxes & fees
8.8/10 Excellent! (3,662 reviews)
Great location. Clean room. Super cozy bed. Friendly, helpful staff! Great stay!

Reviewed on 4 Jan 2026

Hilton Chicago/Magnificent Mile Suites
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is Rp2.319.829 per night from 13 Jan to 14 Jan
Rp2.319.829
Rp3.214.568 total
13 Jan - 14 Jan
includes taxes & fees
8.4/10 Very Good! (2,450 reviews)
Nice hotel, loved all the holiday decor in the lobby and the giant gingerbread Chicago. The historic decor around the hotel is also very interesting. The game area in the lobby was very much appreciated and was a great spot to hang out. The food and drinks at Herb and Kitchen was very overpriced ...

Reviewed on 1 Jan 2026

Hilton Chicago
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is Rp2.388.463 per night from 13 Jan to 14 Jan
Rp2.388.463
Rp3.222.318 total
13 Jan - 14 Jan
includes taxes & fees
8.4/10 Very Good! (2,227 reviews)
Room was very clean and staff was great

Reviewed on 6 Jan 2026

Palmer House a Hilton Hotel
See all 4,745 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 , 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.

Popular places to visit

Northerly Island Park showing a city, a river or creek and views

Northerly Island Natural Area

Bird life, paved paths and a built-in music venue give one of Chicago’s newest green spaces much to offer to nature lovers, exercisers and music fans.

Northerly Island Natural Area
Olmec Head No 8 which includes outdoor art

Olmec Head No 8

Gifted by the government of Veracruz, Mexico, this colossal stone replica greets and educates visitors to the Field Museum of Natural History.

Olmec Head No 8

Things to do

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

Rp411.380
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

Rp1.775.500
per adult
88% of travellers recommend
Chicago C3® by CityPASS®
Art Institute of Chicago

Art Institute of Chicago

Rp670.000
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.