Near South Side Holidays

Book a Hotel + Flight or Car together to unlock savings

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

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

Top hotels in Near South Side

Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
The price is 4.689.054 ₫ per night from 2 Jul to 3 Jul
4.689.054 ₫
6.348.311 ₫ total
2 Jul - 3 Jul
includes taxes & fees
9.2/10 Wonderful! (1,095 reviews)
"Still-attractive hotel despite being the older of the two hotels next to McCormick Place with excellent beds, adequate space, good facilities. It is a very good choice next to the convention centre given its location and cleanliness. The staff were very helpful."

Reviewed on 2 Jun 2026

Hyatt Regency McCormick Place 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 3.673.453 ₫ per night from 30 Jun to 1 Jul
3.673.453 ₫
4.367.367 ₫ total
30 Jun - 1 Jul
includes taxes & fees
8/10 Very Good! (10,171 reviews)
"Good spot. Nice staff. Great location."

Reviewed on 5 Jun 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is 4.002.563 ₫ per night from 28 Jun to 29 Jun
4.002.563 ₫
4.758.647 ₫ total
28 Jun - 29 Jun
includes taxes & fees
7.8/10 Good! (1,518 reviews)
"Clean room"

Reviewed on 3 Jun 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,635 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

Soldier Field

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
McCormick Place

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
Adler Planetarium and Astronomy Museum

Adler Planetarium and Astronomy Museum

You can spend an afternoon studying the exhibits at Adler Planetarium and Astronomy Museum during your travels in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Adler Planetarium and Astronomy Museum