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.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 5 - Aug 11
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
7.6/10 Good! (6,658 reviews)
The room was small and the bathroom was extremely small with no bathroom vanity. The TV was also small for the size of the room

Reviewed on May 15, 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 31 - Aug 4
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
8.4/10 Very Good! (1,003 reviews)
Had an amazing time! Room cleaners were very sweet and

Reviewed on May 6, 2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 4 - Jul 10
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
9.2/10 Wonderful! (3,494 reviews)
Location was fantastic and the property is beautiful!

Reviewed on May 15, 2024

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 1 - Aug 4
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
9.2/10 Wonderful! (96 reviews)
Outstanding service and facility.

Reviewed on Jan 10, 2024

W Chicago - Lakeshore

W Chicago - Lakeshore

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 4 - Jul 10
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
8.2/10 Very Good! (1,001 reviews)
Staff very friendly and helpful. Rooms were good. No coffee makers in rooms which is a bit different but each morning complimemtary coffee was available in the lobby. Really good location for us and we would highly reccommend.

Reviewed on May 14, 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 May 27 to May 28
$167
$196 total
includes taxes & fees
May 27 - May 28
7.6/10 Good! (6,728 reviews)
"I really liked how clean the room was."

Reviewed on May 14, 2024

Congress Plaza Hotel
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $105 per night from May 27 to May 28
$105
$138 total
includes taxes & fees
May 27 - May 28
7.6/10 Good! (2,578 reviews)
"Very clean"

Reviewed on May 14, 2024

Warwick Allerton - Chicago
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $153 per night from May 27 to May 28
$153
$205 total
includes taxes & fees
May 27 - May 28
8.6/10 Excellent! (1,001 reviews)
"We had a wonderful time in Chicago! This property was located in such a great area and easy walking to all the things we wanted to do...and eat. :)"

Reviewed on May 10, 2024

The Westin Michigan Avenue Chicago
See all 4,157 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 $604, 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 Chicago Shoreline Adventure Boat Tour

Chicago Shoreline Adventure Boat Tour

$90
Per adult
Chicago Shoreline Adventure Boat Tour
Image for Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour

Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour

$7
Per adult
Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour
Image for Chicago's Ultimate City Bike Tour

Chicago's Ultimate City Bike Tour

$55
Per adult
Chicago's Ultimate City Bike 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.