South Chicago Packages (Flight + Hotel)
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ฿27,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
฿61,323
per person
16 Dec - 21 Dec
found 14 hours ago
Return flight included
Bangkok (BKK) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
Beautiful property! Great location! Breakfast was amazing every day at no charge. Will definitely go back.
Reviewed on 11 Oct 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
฿63,407
per person
16 Dec - 21 Dec
found 14 hours ago
Return flight included
Bangkok (BKK) to Chicago (ORD)
9.4/10 Exceptional! (3,877 reviews)
I was disappointed. The location is great but the rooftop bar was disappointing and the rooms were subpar.
Reviewed on 11 Oct 2026
Where to stay in South Chicago
Find the best South Chicago areas and neighborhoods for the activities you enjoy most. Learn more about South Chicago
Downtown Chicago
4 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.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Top hotels in South Chicago
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
฿3,893
฿4,628 total
10 Nov - 11 Nov
includes taxes & fees
8/10 Very good! (10,162 reviews)
"The building is so beautiful and so iconic. The wood is as rich as Chicago’s history."
Reviewed on 11 Oct 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
฿5,102
฿6,065 total
25 Oct - 26 Oct
includes taxes & fees
8.8/10 Excellent! (5,527 reviews)
"A/c didn’t work so room was a little toasty. Otherwise excellent location, amazing views. Clean room"
Reviewed on 11 Oct 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
฿4,794
฿5,699 total
1 Nov - 2 Nov
includes taxes & fees
8/10 Very good! (2,478 reviews)
"Nice and quiet"
Reviewed on 11 Oct 2026
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 South Chicago holiday package cost?
Live it up in South Chicago from just ฿61,323. Choose from a wonderful selection of hotels, flights and rental cars to suit your travel style. You can score even more discounts when you add a few sightseeing activities to your holiday package.
How do I get a cheap travel package to South Chicago?
Combine your flights and hotels, toss in extras such as activities or a rental car, and save with a South Chicago holiday package. You won't just pick up impressive discounts on your escape — you'll have lots of choice within your reach too. When you book through Expedia, you can select from more than 550 partner airlines and 1,000,000 hotels around the globe. Your dream holiday starts right here, right now!
Where should I stay in South Chicago?
With so much to do in South Chicago, it's a good idea to secure a room in a hotel close to its attractions. Calumet Beach, Calumet Park and Bronzeville Childrens Museum are some interesting ones to put on your must-see list.
How far in advance should I book my South Chicago holiday?
While not all airlines release ticket prices early, it's usually possible to compare international fares on Expedia up to 12 months in advance. This is the time you can bag some fantastic bargains. If you're purchasing tickets last minute, you might get lucky. Sometimes the cheapest prices emerge just weeks before departure.
What does an Expedia South Chicago travel package include?
From hotels and flights to car rentals, Expedia can help you craft a South Chicago package that fits you. Heading away for a week or longer? Consider a flight, rental car and hotel bundle. If you're taking a quick break, a hotel and flight deal could suit you better. Tours and activities can be added after you've booked. Our packages make it a cinch to plan and save.
What should I know before booking a South Chicago travel package?
You'll save big with an Expedia travel package. Bundle your airfares, rental cars and hotels and pick up fantastic discounts. You're not restricted to hotels, though. We've got island resorts, cosy city apartments and everything in between!
Can I choose my airline with a South Chicago Expedia holiday package?
Yes, of course. Expedia has access to more than 550 airline partners around the world, so fly with the carrier that best fits your budget and travelling style.
If I'm not able to travel, can I cancel my South Chicago holiday package?
If your holiday plans in South Chicago have changed, it's good to know that it's possible to cancel your booking. If you made your booking less than 24 hours ago, you may be eligible for a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may impose a cancellation fee. To find out more, check our Customer Service Portal.
Stay near popular South Chicago attractions
Mahalia Jackson Residence
You can find out about the history of Chicago with a stop at Mahalia Jackson Residence. Experience the area's entertainment choices and live music.
Things to do
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.