Near South Side Vacations from ￥187,807

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The Latest Near South Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago O'Hare Rosemont

Embassy Suites by Hilton Chicago O'Hare Rosemont

4 out of 5
Price was ￥210,169, price is now ￥187,807 per person
￥187,807
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
8.8/10 Excellent! (1,208 reviews)
Room is spacious, good breakfast, airport shuttle sevice. Only complaint is the atrium is very noisy at night and can be disruptive if your room is on a lower floor

Reviewed on Dec 30, 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was ￥221,254, price is now ￥187,926 per person
￥187,926
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Staff was excellent, roim was nice

Reviewed on Dec 30, 2025

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 out of 5
Downtown Chicago
Price was ￥220,623, price is now ￥190,646 per person
￥190,646
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
8.6/10 Excellent! (1,761 reviews)
The room was clean. The staff was very nice and helpful. Breakfast was worth the price, the freshness and the portions were nice. There were a few maintenance issues in the room, that need to be taken care of, but didn't impact our stay that much. It was a great location, easy to walk to different museums and restaurants.

Reviewed on Jan 1, 2026

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Price was ￥228,222, price is now ￥199,423 per person
￥199,423
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.2/10 Wonderful! (1,404 reviews)
Room was great, staff was incredible and so friendly! Location was awesome-restaurant was closed during our stay so -1 Star but would recommend.

Reviewed on Dec 21, 2025

Hilton Garden Inn Chicago / Oak Brook

Hilton Garden Inn Chicago / Oak Brook

3 out of 5
Yorkfield
Price was ￥221,086, price is now ￥198,414 per person
￥198,414
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
8.2/10 Very Good! (1,003 reviews)
Clean room, friendly staff and great location for our needs!

Reviewed on Dec 27, 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

Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥21,671 per night from Jan 17 to Jan 18
￥21,671
￥30,029 total
Jan 17 - Jan 18
includes taxes & fees
8.4/10 Very Good! (2,445 reviews)
Best option for us while attending an event at McCormick place, with ability to park in public parking that is cheaper than the hotel parking!

Reviewed on Dec 30, 2025

Hilton Chicago
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 ￥13,977 per night from Feb 1 to Feb 2
￥13,977
￥16,407 total
Feb 1 - Feb 2
includes taxes & fees
8.8/10 Excellent! (3,613 reviews)
Clean room , great location.

Reviewed on Dec 30, 2025

Hilton Chicago/Magnificent Mile Suites
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥22,312 per night from Jan 17 to Jan 18
￥22,312
￥30,102 total
Jan 17 - Jan 18
includes taxes & fees
8.4/10 Very Good! (2,195 reviews)
Our stay was absolutely perfect. The room was clean. The staff was amazing! The decorations were festive and the pool was spotless warm and very very family friendly!!

Reviewed on Dec 29, 2025

Palmer House a Hilton Hotel
See all 4,731 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 ￥187,807, 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

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
Adler Planetarium and Astronomy Museum showing modern architecture

Adler Planetarium and Astronomy Museum

4.5/5(186 reviews)

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

River tour boat in Chicago

Architecture River Tour

￥6,839
per adult
96% of travellers recommend
Architecture River Tour
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,827
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥6,310
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture 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.