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

4 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

Top hotels in Near South Side

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 4.502.822 ₫ per night from 27 Mar to 28 Mar
4.502.822 ₫
5.286.125 ₫ total
27 Mar - 28 Mar
includes taxes & fees
8/10 Very Good! (9,895 reviews)
We mainly go to Chicago for medical appointments and it is *so awesome* that you can actually open the windows here.That is the main reason we chose it. Because Dad has cancer we aired it out and then ran our own air purifier. No bad smells or anything, we're just being cautious because of his health. ...

Reviewed on 27 Feb 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is 2.943.691 ₫ per night from 4 Mar to 5 Mar
2.943.691 ₫
4.189.913 ₫ total
4 Mar - 5 Mar
includes taxes & fees
9.4/10 Exceptional! (3,428 reviews)
Great breakfast and friendly staff

Reviewed on 28 Feb 2026

Hotel Riu Plaza Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is 2.876.803 ₫ per night from 5 Mar to 6 Mar
2.876.803 ₫
3.377.078 ₫ total
5 Mar - 6 Mar
includes taxes & fees
8.6/10 Excellent! (5,698 reviews)
The room was clean but phone was left in room even thought no land line. Curtain hooks were not properly functioning. Being near casino, we were a little crowded and full of all kinds of people and a tad noisy. All and all it was decent place for a one night stay. Also, no complimentary water or ...

Reviewed on 1 Mar 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,754 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 1null000null000 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

McCormick Place showing a high rise building and a city

McCormick Place

During your trip, find out what's happening in McCormick Place, a top convention centre in Chicago. Discover the acclaimed art galleries and notable monuments in this vibrant area.

McCormick Place
Soldier Field which includes a high-rise building, a city and modern architecture

Soldier Field

Catch an event at Soldier Field during your trip to Chicago. Stroll along the lakeside or visit the notable monuments in this vibrant area.

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

Northerly Island Natural Area

You can take time to visit Northerly Island Natural Area during your travels to Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.

Northerly Island Natural Area