Near South Side Trips (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 showing 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.

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Magnificent Mile - River North

Magnificent Mile

Michigan Avenue and Chicago Water Tower are just a few worthwhile attractions to visit in Magnificent Mile. Travelers also love the fascinating museums, panoramic lake views, and popular shops.

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The Loop - Downtown which includes a river or creek

The Loop

4/5(1 area review)

Michigan Avenue and Lake Michigan are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops, and acclaimed art galleries.

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Top hotels in Near South Side

Sonder South Wabash
Sonder South Wabash
3.5 out of 5
1419 South Wabash Avenue, Chicago, IL
The price is P7,699 per night from 30 Apr to 1 May
P7,699
P9,038 total
includes taxes & fees
Apr 30 - May 1
8.8/10 Excellent! (475 reviews)
Nice but could be better
"The room was prettt clean but there were several dusty areas. The beds were not comfortable and very low to the ground. The sofa sleeper was only comfortable if you slept on top of a comforter."

Reviewed on Apr 20, 2025

Sonder South Wabash
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 P8,292 per night from 1 May to 2 May
P8,292
P9,734 total
includes taxes & fees
May 1 - May 2
8.2/10 Very Good! (3,922 reviews)
"Súper limpio el personal muy agradable lo recomiendo un 100 por ciento"

Reviewed on Apr 21, 2025

Embassy Suites by Hilton Chicago Downtown River North
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is P10,203 per night from 11 May to 12 May
P10,203
P13,641 total
includes taxes & fees
May 11 - May 12
8.8/10 Excellent! (2,073 reviews)
"My wife & I spent a 4 day weekend at the Swissotel & it was the best customer service we’ve ever experienced. The staff, specifically Kia, Joseph, and Bailey were more than accommodating & friendly. The hotel is right on the riverfront & extremely close to restaurants & shops. We can’t wait to go ..."

Reviewed on Apr 22, 2025

Swissotel - Chicago
See all 4,159 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 vacation package cost?
The most affordable Near South Side package is , so your dream vacation 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 vacation packages mean plenty of savings for the savvy traveler. 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 favorites among many travelers.
How far in advance should I book my Near South Side vacation?
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 vacation 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 vacation package?
We totally get it — life can throw you the odd curveball. If you’ve booked a Near South Side vacation 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

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Northerly Island Park featuring views, a city and a river or creek

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 showing modern architecture

Adler Planetarium and Astronomy Museum

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: Field Museum of Natural History Ticket or VIP Tour

Chicago: Field Museum of Natural History Ticket or VIP Tour

P1,663
per adult
88% of travellers recommend
Chicago: Field Museum of Natural History Ticket or VIP Tour
Field Museum of Natural History All-Access Pass

Field Museum of Natural History All-Access Pass

P2,352
per adult
Field Museum of Natural History All-Access Pass
Field Museum of Natural History Ticket with Self-Guided Audio Tour

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

P3,479
per adult
100% of travellers recommend
Field Museum of Natural History Ticket with Self-Guided Audio 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.