Near South Side Vacation Packages
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Top Holiday Package Deals in Near South Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,720
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Great spot for a few days stay to get the full city experience. Breakfast room is something else! I wish the rooftop bar were open only to hotel guests. It's awesome but overwhelmed by young folks so impossible to be spontaneous or even get a reservation. Must be a hot hangout.
Reviewed on Sep 8, 2026
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
4 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.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
Near South Side Hotel Deals
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
Fully refundableReserve now, pay when you stay
CA $316
CA $417 total
Sep 9 - Sep 10
includes taxes & fees
9.2/10 Wonderful! (1,400 reviews)
"That sounds like an incredibly frustrating and chaotic stay, and it is completely unacceptable for a high-end hotel to drop the ball like that. When you pay a premium price, you expect seamless service, not a battle just to get a blanket or ride the elevator.Worse than the poor service, having a ..."
Reviewed on Sep 7, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $166
CA $197 total
Sep 9 - Sep 10
includes taxes & fees
8/10 Very good! (10,318 reviews)
"I loved the location. It was perfect for seeing the city sights and getting to them on public transit.. I thought the front desk was unwelcoming and acted I different to concerns. Other staff were appropriately accommodating and helpful."
Reviewed on Sep 8, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $235
CA $280 total
Oct 5 - Oct 6
includes taxes & fees
8/10 Very good! (2,183 reviews)
"I stayed there two nights the first night we checked in at 11 PM and we had no air conditioning and we didn’t realize it until about 2 AM. We were sweating., I could not sleep all night. The next day they got the air fixed and the ceiling. It was so sickening. It was peeling and almost looked like ..."
Reviewed on Sep 8, 2026
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 CA $1,287, 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.
Stay near popular Near South Side attractions
Photo by © City of Chicago
Soldier Field
8.8/10 (7,063 reviews)
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Photo by © Cesar Russ Photography
McCormick Place
8.8/10 (9,822 reviews)
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.
Photo by City Of Chicago
Field Museum of Natural History
9.4/10 (1,744 reviews)
Dinosaur bones, rare gems and real Egyptian mummies are among the displays at this family favorite.
Adler Planetarium and Astronomy Museum
8.8/10 (248 reviews)
Opportunities for fun, learning and wonder abound at this historic and state-of-the-art museum on the pretty shore of Lake Michigan.
Northerly Island Natural Area
8.6/10 (28 reviews)
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
Commune with nature and explore the great outdoors at Northerly Island during your travels in Chicago. Experience the acclaimed art scene and entertainment choices in this vibrant area.
Wintrust Arena
8.0/10 (70 reviews)
Catch an event at Wintrust Arena during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.
Arie Crown Theater
8.0/10 (9 reviews)
You can enjoy a show at Arie Crown Theater on your trip to Chicago. Experience the fascinating museums and acclaimed art scene in this vibrant area.
Things to do
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $56
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.