Near South Side Vacations from ￥265,338

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The Latest Near South Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,055 reviews)
Most convenient hotel at O’Hare

Reviewed on Jul 27, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
The hotel was nice, staff were friendly and the overall stay was excellent and convenient to walk.

Reviewed on Jul 28, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
Sep 9 - Sep 16
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
The hotel is ok. There’s one actual restaurant and the food is average. Outside of that you can walk to the pier. The main advantage is being on the pier and the hotel really rides that as their main selling point because they can’t stand on their own too much. I stayed recently and had an extra 197 charged to my card that wasn’t on my receipt and I called to see what that was from. The guy who answered the phone answered with “hi. What do you need”. And when I said I wanted to confirm the charge he said what it was and then hung up on me. I’ve never had a hotel be that unfriendly. I work customer service so I know a lot of people can not be great on the phone. But that was unprompted and flat out rude.

Reviewed on Jul 29, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 3 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
The hotel is in a fantastic location. Staff service was very high quality and the lobby and common areas were very clean and well organized. Gym was modern, big and clean. The actual room had some marks on the walls and a buzzy air handling vent in the master. An automated lighting system that was a bit dim and difficult to use. We would stay again. Mini bar and snacks were high quality. We would stay again.

Reviewed on Jul 29, 2025

Wrigleyville Suites

Wrigleyville Suites

2 out of 5
Lakeview
per person
Sep 18 - Sep 22
found 9 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.2/10 Wonderful! (7 reviews)
Excellent location and very clean! Would stay again!

Reviewed on Jul 25, 2025

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

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

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 ￥19,945 per night from Aug 18 to Aug 19
￥19,945
￥23,413 total
Aug 18 - Aug 19
includes taxes & fees
7.8/10 Good! (9,038 reviews)
"This was a nice option for my wife and I . Nice location plenty of dining with in walking distance. Highly recommend this hotel"

Reviewed on Jul 29, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is ￥34,002 per night from Aug 24 to Aug 25
￥34,002
￥44,666 total
Aug 24 - Aug 25
includes taxes & fees
9/10 Wonderful! (2,137 reviews)
"Elevator"

Reviewed on Jul 28, 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥21,329 per night from Aug 24 to Aug 25
￥21,329
￥25,038 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (2,535 reviews)
"Staff were friendly. Bell attendants were accommodating and helpful! Facilities were clean and tidy. I would definitely stay there again!"

Reviewed on Jul 29, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,610 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 ￥265,338, 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

Soldier Field featuring a skyscraper, modern architecture and a city

Soldier Field

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

Soldier Field
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

Field Museum of Natural History All-Access Pass

Field Museum of Natural History All-Access Pass

￥6,010
per adult
Field Museum of Natural History All-Access Pass
Chicago Fire FC Football Game at Soldier Field

Chicago Fire FC Football Game at Soldier Field

￥2,010
per adult
Chicago Fire FC Football Game at Soldier Field
Field Museum of Natural History Ticket with Self-Guided Audio Tour

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

￥9,284
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.