Near South Side Packages (Flight + Hotel)

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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

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

Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is ฿6,839 per night from 1 Jul to 2 Jul
฿6,839
฿9,092 total
1 Jul - 2 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 ฿4,558 per night from 29 Jun to 30 Jun
฿4,558
฿5,419 total
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (10,166 reviews)
"Apparently it's haunted and I had the room across the hall from the haunted room. I didn't know this until my third night there, but it was quiet and calm."

Reviewed on 4 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 ฿4,966 per night from 28 Jun to 29 Jun
฿4,966
฿5,904 total
28 Jun - 29 Jun
includes taxes & fees
7.8/10 Good! (1,510 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 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

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
Adler Planetarium and Astronomy Museum

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
Northerly Island Natural Area

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

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

฿874
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago CityPASS: Admission to Top 5 Chicago Attractions

Chicago CityPASS®: Experience 5 must-see attractions

฿4,715
per adult
94% of travellers recommend
Chicago CityPASS®: Experience 5 must-see attractions
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

฿3,569
per adult
90% of travellers recommend
Chicago C3® by CityPASS®
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.