South Side Vacations from ￥562,288

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The Latest South Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was ￥642,018, price is now ￥562,288 per person
￥562,288
per person
Aug 8 - Aug 14
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
This was a very clean and nice hotel. I enjoyed the room.

Reviewed on Jul 6, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥836,330, price is now ￥715,305 per person
￥715,305
per person
Aug 8 - Aug 14
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
The best hotel we have ever stayed at!

Reviewed on Jul 6, 2026

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Downtown Chicago
Price was ￥640,292, price is now ￥587,434 per person
￥587,434
per person
Aug 8 - Aug 14
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (3,109 reviews)
The air conditioner and the refrigerator was not working in the room . Called to have it serviced three times.

Reviewed on Jul 6, 2026

voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG

3.5 out of 5
Downtown Chicago
Price was ￥637,702, price is now ￥586,868 per person
￥586,868
per person
Aug 8 - Aug 14
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.8/10 Excellent! (3,802 reviews)
Very clean, friendly staff. Madison with Voco helped make it a great stay. Would stay here again.

Reviewed on Jul 6, 2026

Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was ￥601,742, price is now ￥563,546 per person
￥563,546
per person
Aug 8 - Aug 14
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (2,139 reviews)
LONI, at the front desk was AMAZING!! from the time we checked in, until we left, she was absolutely great. The hotel was so nice, clean, and in a great location, close to everything!! I'll definitely stay here again, when traveling to Chicago! THE KINZIE HOTEL gets 5 stars from me!

Reviewed on Jul 6, 2026

Where to stay in South Side

Find the best South Side areas and neighborhoods for the activities you enjoy most. Learn more about South Side
A classical building with a dome and columns, featuring Charlie Brown exhibit banners.

Hyde Park

3 out of top 10 points of interest in this area
4.5/5(136 area reviews)

Hyde Park is noteworthy for its museums, and you can make a stop at top attractions like Lake Michigan and Griffin Museum of Science and Industry.

Find hotels in Hyde Park

Find the Best South Side Vacation Packages

South Side Hotel Deals

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
7353 S Cicero Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥23,088 per night from Jul 8 to Jul 9
￥23,088
￥28,717 total
Jul 8 - Jul 9
includes taxes & fees
8.2/10 Very Good! (1,016 reviews)
"Clean, good neighborhood close to CTa Orange Line, staff was helpful, courteous property was well maintained air conditioning was on point very cold for the extreme heat"

Reviewed on Jul 5, 2026

Holiday Inn Chicago – Midway Airport S by IHG
Motel 6 - Chicago, IL

Motel 6 - Chicago, IL

2 out of 5
10022 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥13,938 per night from Aug 3 to Aug 4
￥13,938
￥16,363 total
Aug 3 - Aug 4
includes taxes & fees
7.4/10 Good! (390 reviews)
"If you want a cheap and affordable room. Motel 6 is the best option to go with. Clean room, helpful staff. Only downside was the ice machine was out of order for some reason."

Reviewed on Jul 5, 2026

Motel 6 - Chicago, IL
Jaslin Hotel

Jaslin Hotel

3 out of 5
261 West Cermak Rd Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥18,823 per night from Jul 7 to Jul 8
￥18,823
￥22,376 total
Jul 7 - Jul 8
includes taxes & fees
9/10 Wonderful! (1,243 reviews)
"Great"

Reviewed on Jul 6, 2026

Jaslin Hotel
See all 456 properties in 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.

Stay near popular South Side attractions

A cityscape with historic buildings, a prominent church, and a view of the ocean.

University of Chicago

8.6/10 (3,689 reviews)
Take a campus tour or just explore the area around University of Chicago, a top university in Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.
See properties

What to do in South Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥3,887
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,853
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

￥6,398
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in South Side

Frequently asked questions

How much does a South Side vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in South Side from just ￥562,288. And the more you bundle, the more you save. The getaway of your dreams has never been so affordable.
How do I get a cheap travel package to South Side?
Book everything in the one place with our South Side vacation packages. You'll find deals on flights, hotels and more that'll keep your pocket happy and your adventurous side busy. And, with more than 550 air carriers and 1,000,000 hotels throughout the world to pick from, you'll have the flexibility to mix and match all you want.
What are the top hotels in South Side?
When it comes to properties in Carville, Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton are a couple of favorites. If you're considering heading to Chatham Fields, The Whitehall Hotel and Hyatt Regency Chicago are waiting to welcome you.
How far in advance should I book my South Side vacation?
While not all airlines advertise ticket prices early, it's usually possible to look up international flights on Expedia up to a year in advance. This is the time you can bag some incredible deals. If you're purchasing tickets last minute, there's a chance you could get lucky. Sometimes the lowest prices become available a few weeks prior to departure.
What does an Expedia South Side travel package include?
Expedia has everything you need to book your South Side escape, but what your package looks like is up to you. Choose from a combination of rental cars, hotels and flights. Searching for some activities to keep you busy? Once you've made your booking, you can add them on too. Whatever your style or budget, there's a package deal to suit your needs.
What should I know before booking a South Side travel package?
Discover deals that suit your budget with an Expedia package. Flights, hotels, rental cars — we're a one-stop shop for all of them. You'll save precious cash just for combining your bookings. Whether you're embarking on a ski trip or relaxing on a sunny beach, your perfect getaway is only clicks away.
Can I choose my airline with a South Side Expedia vacation package?
Most definitely. Expedia has over 550 partner airlines to choose from all over the world. With so many choices, finding the right carrier to bring you to South Side will be a snap.
If I'm not able to travel, can I cancel my South Side vacation package?
You can. We get that even the best-laid plans can go awry, so we're here to help if you have to make changes to your South Side vacation package. It may be possible to amend or cancel your itinerary for free if you've booked within 24 hours. Your airline, hotel or car rental company may charge you a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for more information. Also, check your itinerary for the nitty-gritty on change fees.

Explore a world of travel with Expedia

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