South Side Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ฿27,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top South Side Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was ฿261,909, price is now ฿237,985 per person
฿237,985
per person
30 Aug - 5 Sept
found 1 day ago
Return flight included
Bangkok (DMK) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Location

Reviewed on 10 Jul 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ฿293,029, price is now ฿261,820 per person
฿261,820
per person
30 Aug - 5 Sept
found 1 day ago
Return flight included
Bangkok (DMK) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
I love Trump hotels the absolute BEST

Reviewed on 10 Jul 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was ฿303,942, price is now ฿273,427 per person
฿273,427
per person
30 Aug - 5 Sept
found 1 day ago
Return flight included
Bangkok (DMK) to Chicago (ORD)
9.8/10 Exceptional! (1,008 reviews)
The most helpful staff. The most comfortable bed. The most luxurious bathroom. The Peninsula is unrivaled amongst the five-star hotels. Cannot wait to return yet again!

Reviewed on 5 Jul 2026

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was ฿284,210, price is now ฿257,882 per person
฿257,882
per person
30 Aug - 5 Sept
found 1 day ago
Return flight included
Bangkok (DMK) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Fantastic staff, beautiful property. Highly recommend the club lounge

Reviewed on 10 Jul 2026

Nobu Hotel Chicago

Nobu Hotel Chicago

5 out of 5
Downtown Chicago
Price was ฿285,807, price is now ฿264,595 per person
฿264,595
per person
30 Aug - 5 Sept
found 1 day ago
Return flight included
Bangkok (DMK) to Chicago (ORD)
9.4/10 Exceptional! (879 reviews)
Stunning hotel with really attentive staff, located in the heart of Chicago's West Loop neighborhood. You are surrounded by a ton of award-winning restaurants, shopping and also close to public transit. Rooms are spacious and are themed in a minimalistic Japanese onsen-style esthetic. We loved our stay here, though there are a few things to mention that made our stay less than a perfect 10. The bathroom is fully painted in black. Looks great, but terrible for styling your hair, if you have dark colored hair. Poor lighting concepts throughout the room and bathroom in general, which made it terrible for getting ready any time of the day. Closet area was dark, not great for getting dressed. Bedroom area was dark, not great for reading a book. Desk area is dark, not great for working remotely. Bathroom lighting is dark, not great if you are a woman trying to put on makeup. Housekeeping was fantastic and really knew how to personalize your stay, but they still knocked on the door when we had the "do not disturb" light on, which was very bothersome and woke us up a couple of times.

Reviewed on 6 Jul 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
3/5(1 area review)

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

Top hotels in South Side

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 ฿4,334 per night from 10 Aug to 11 Aug
฿4,334
฿5,421 total
10 Aug - 11 Aug
includes taxes & fees
8.2/10 Very good! (1,032 reviews)
"I had a TERRIBLE experience at a stinking Extended Stay and needed a last minute room. This hotel was excellent. I booked the room here, and checked in within 20 minutes. The room was clean and the housekeeper was outstanding. Thank you."

Reviewed on 10 Jul 2026

Holiday Inn Chicago – Midway Airport S by IHG
Jaslin Hotel

Jaslin Hotel

3 out of 5
261 West Cermak Rd Chicago IL
The price is ฿5,345 per night from 9 Aug to 10 Aug
฿5,345
฿6,355 total
9 Aug - 10 Aug
includes taxes & fees
9/10 Wonderful! (1,249 reviews)
"Very friendly staff, helping and supporting."

Reviewed on 11 Jul 2026

Jaslin Hotel
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 ฿2,876 per night from 3 Aug to 4 Aug
฿2,876
฿3,376 total
3 Aug - 4 Aug
includes taxes & fees
7.4/10 Good! (395 reviews)
"This was a solo backpack trip for me so I don’t mind the hotel - there was no elevator working, the floors/ ground leading to the door of the rooms were dirty and unstable as in not smooth- I personally don’t mind marijuana smoke but if you are sensitive to it you may have a problem - I will say ..."

Reviewed on 8 Jul 2026

Motel 6 - Chicago, IL
See all 458 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 theatre scene in this vibrant area.
See properties

Frequently asked questions

How much does a South Side holiday package cost?
Choose from any combination of flights, hotels and car rentals, and you can be holidaying in South Side from just ฿237,985. 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 holiday 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 favourites. 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 holiday?
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 holiday 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 holiday 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 holiday 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.