Near South Side Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ฿4,531 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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

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 ฿5,766 per night from 4 Aug to 5 Aug
฿5,766
฿6,769 total
4 Aug - 5 Aug
includes taxes & fees
7.8/10 Good! (8,938 reviews)
"Very convenient location. Easy check-in, even with a very crowded lobby. Polite staff."

Reviewed on 1 Aug 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
The price is ฿6,631 per night from 1 Sept to 2 Sept
฿6,631
฿8,825 total
1 Sept - 2 Sept
includes taxes & fees
9/10 Wonderful! (2,160 reviews)
"Great view"

Reviewed on 2 Aug 2025

InterContinental Chicago Magnificent Mile by IHG
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 ฿4,670 per night from 17 Aug to 18 Aug
฿4,670
฿5,482 total
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (2,562 reviews)
"Nice clean hotel, good location."

Reviewed on 2 Aug 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,620 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

Field Museum of Natural History showing a city

Field Museum of Natural History

4.5/5(27 reviews)

Dinosaur bones, rare gems and real Egyptian mummies are among the displays at this family favorite.

Field Museum of Natural History
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
Adler Planetarium and Astronomy Museum featuring modern architecture

Adler Planetarium and Astronomy Museum

3.5/5(2 reviews)

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

Things to do

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

Chicago C3® by CityPASS®

฿3,439
per adult
86% of travellers recommend
Chicago C3® by CityPASS®
Field Museum of Natural History Ticket with Self-Guided Audio Tour

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

฿2,048
per adult
100% of travellers recommend
Field Museum of Natural History Ticket with Self-Guided Audio Tour
Bike Tour

Chicago's Ultimate City Bike Tour

฿1,946
per adult
100% of travellers recommend
Chicago's Ultimate City Bike 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.