Near South Side Vacations

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Your Near South Side Vacation

Book a vacation package to Near South Side and get set to immerse yourself in its history, walking and culture. However you want to spend your time in this lakeside neighborhood, there are plenty of opportunities for relaxation and fun. Your trip to Near South Side wouldn't be complete without stopping by leading attractions nearby such as Millennium Park, Willis Tower and Art Institute of Chicago. Don't just dream it — turn it into reality! Secure your ideal Near South Side vacation with Expedia and enjoy traveling your way.

The Latest Near South Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 5 - Jul 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,005 reviews)
Well kept, great location and friendly staff!

Reviewed on May 31, 2024

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 29 - Aug 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,004 reviews)
Perfect area to go shopping, check out tourist attractions, or relax at the beach. Very convenient area to head to Lakefront Trail as well for a morning run. Staff was helpful and friendly during every interaction. I really loved all the benefits you received through the destination fee. Property was clean and attentive. In a very walkable area and close to public transportation.

Reviewed on Jun 3, 2024

Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 29 - Aug 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,006 reviews)
my stay went really well! staff were friendly and always attentive. housekeeping were really friendly and nice. everything met our needs and the view was nice to see. thank you!

Reviewed on Jun 2, 2024

Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 22 - Aug 25
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8/10 Very Good! (1,731 reviews)
The front desk was rude and didn’t even explain the parking he just said go over there and figure it out. He worked in the afternoon and night

Reviewed on May 31, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 23 - Aug 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,212 reviews)
Bid room but not cleaned nor updated. Late check out is only at 1pm. No room upgrade offered. There was 1 day that room was not serviced until late evening. Good location

Reviewed on Jun 2, 2024

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

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotel + flight trips in Downtown Chicago

Near South Side Hotel Deals

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 $167 per night from Jun 16 to Jun 17
$167
$196 total
includes taxes & fees
Jun 16 - Jun 17
7.6/10 Good! (6,840 reviews)
"Perfect location to museum and restaurants. Good for family and friends"

Reviewed on Jun 3, 2024

Congress Plaza Hotel
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 $211 per night from Jul 1 to Jul 2
$211
$247 total
includes taxes & fees
Jul 1 - Jul 2
8/10 Very Good! (2,350 reviews)
"Loved the location"

Reviewed on Jun 3, 2024

Embassy Suites by Hilton Chicago Downtown River North
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $179 per night from Jun 30 to Jul 1
$179
$210 total
includes taxes & fees
Jun 30 - Jul 1
8.6/10 Excellent! (2,943 reviews)
"Perfect area for walking around chicago even at night. Felt 100 percent safe and the weather mafe for an emalculat trip."

Reviewed on Jun 4, 2024

River Hotel
See all 4,106 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Near South Side vacation package cost?
The most affordable Near South Side package is $344, 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.

Discover the most popular places to visit in Near South Side

Image for McCormick Place

McCormick Place

4.5/5(1,805 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.

McCormick Place
Image for Soldier Field

Soldier Field

4.5/5(1,256 reviews)

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Soldier Field
Image for Shedd Aquarium

Shedd Aquarium

4.5/5(1,675 reviews)

Make time in your itinerary to visit the sea life you'll find at Shedd Aquarium during your visit to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.

Shedd Aquarium

Things to do

Image for Prairie Avenue Haunted History Tour and Ghost Hunt

Prairie Avenue Haunted History Tour and Ghost Hunt

$40
Per adult
Prairie Avenue Haunted History Tour and Ghost Hunt
Image for Chicago's Ultimate City Bike Tour

Chicago's Ultimate City Bike Tour

$55
Per adult
Chicago's Ultimate City Bike Tour
Image for Small Group Lake Michigan Tour

Small Group Lake Michigan Tour

$60
Per adult
Small Group Lake Michigan Tour
See all activities in Chicago

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.