Near South Side Vacations from ￥74,260

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The Latest Near South Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Prospect Heights by IHG

Holiday Inn Express & Suites Prospect Heights by IHG

3 out of 5
Price was ￥86,400, price is now ￥74,260 per person
￥74,260
per person
Dec 23 - Dec 27
found 5 hours ago
Roundtrip flight included
Omaha (OMA) to Chicago (ORD)
18/10 Exceptional! (873 reviews)
Clan quiet room. Comfortable bed. Great staff. Need to upgrade the fitness center

Reviewed on Nov 11, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥368,723, price is now ￥296,398 per person
￥296,398
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
18.8/10 Exceptional! (1,771 reviews)
It was absolutely wonderful. We were upgraded to a suite which was pretty sweet (no pun intended)! At night the surrounding view of the lake along the lakeside of the hotel was spectacular. The Rebar on the mezzanine floor with a live musician playing a saxophone on a Saturday, was a cozy and lively setting. Welcome champagne upon check in was a nice touch. The Terrace 16 restaurant/bar also served scrumptious choices on the menu. Overall, very satisfied with our stay.

Reviewed on Nov 14, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was ￥290,032, price is now ￥249,365 per person
￥249,365
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.2/10 Wonderful! (303 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.

Reviewed on Oct 28, 2025

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥301,902, price is now ￥260,239 per person
￥260,239
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
17.6/10 Exceptional! (3,089 reviews)
Clean room, friendly staff. My one gripe is that the shower door has a gap in it that will cause the water to leak out onto the floor if not careful. Be sure to ask for some extra towels

Reviewed on Nov 16, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was ￥287,985, price is now ￥248,873 per person
￥248,873
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
18.8/10 Exceptional! (1,131 reviews)
Staff was our favorite part! Very very professional and friendly

Reviewed on Nov 14, 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

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 ￥14,713 per night from Nov 25 to Nov 26
￥14,713
￥17,273 total
Nov 25 - Nov 26
includes taxes & fees
8.4/10 Very Good! (5,235 reviews)
Clean room; kind and courteous staff; excellent breakfast and happy hour included

Reviewed on Nov 10, 2025

Embassy Suites by Hilton Chicago Downtown River North
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 ￥16,348 per night from Nov 24 to Nov 25
￥16,348
￥23,056 total
Nov 24 - Nov 25
includes taxes & fees
8.4/10 Very Good! (2,060 reviews)
Great location, great staff!

Reviewed on Nov 16, 2025

Palmer House a Hilton Hotel
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 ￥15,081 per night from Dec 7 to Dec 8
￥15,081
￥17,704 total
Dec 7 - Dec 8
includes taxes & fees
8.8/10 Excellent! (3,290 reviews)
I loved that everything was in walking distance. It was very clean. The hospitality service was excellent! Very kind and friendly!

Reviewed on Nov 14, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,680 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 ￥74,260, 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

River tour boat in Chicago

Architecture River Tour

￥7,445
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

￥6,717
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,749
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.