South Chicago Holidays

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Your South Chicago Holiday

South Chicago is calling! Whatever type of getaway you're organising, get ready to discover the best of this neighbourhood with a South Chicago holiday package. When it's time to get out and explore, you'll find lots of big-name attractions nearby including Calumet Park, Calumet Beach and Munson Beach. Visit one, two (or even all!) during your trip to South Chicago. Expedia is here to put your plans into action. Book your ideal South Chicago holiday today.

Our guide on 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
A busy city street with tall buildings, a bus, and cars.

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.

Find hotels in Downtown Chicago
A river with yellow boats, a bridge, and tall buildings.

The Loop

Striking architecture, urban park space and countless entertainment options all make The Loop one of the most memorable spots in the city.

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A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

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A city street with a train passing overhead, cars, pedestrians, and a red brick building.

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.

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A nighttime cityscape with fireworks over a body of water, a Ferris wheel, and illuminated buildings.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).

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Our pick of the best South Chicago Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
AU$178
8 Sept - 9 Sept
includes taxes & fees
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
AU$241
30 Aug - 31 Aug
includes taxes & fees
8/10 Very good! (1,973 reviews)
"Well I thought gettinso I got the hotel room through Expedia for $265. Thought I got a good deal. Oh no then the property decided to charge another $150 for fees. Which makes no sense to me. Was definitely not that great of a hotel. So this was a completely ridiculous hotel stay. Won't be back."

Reviewed on 10 Aug 2026

The Chicago Hotel Collection Ambassador Gold Coast
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

171 W Randolph St Chicago IL
Fully refundableReserve now, pay when you stay
AU$346
7 Sept - 8 Sept
includes taxes & fees
The Allegro Royal Sonesta Hotel Chicago Loop
See all 4,253 properties in South Chicago
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays
family friendly holidays
Family Friendly Holidays
Family Friendly Holidays
golf holidays
Golf Holidays
Golf Holidays
luxury holidays
Luxury Holidays
Luxury Holidays
romantic holidays
Romantic Holidays
Romantic Holidays
ski holidays
Ski Holidays
Ski Holidays
honeymoon holidays
Honeymoon Holidays
Honeymoon Holidays
pet friendly holidays
Pet-friendly Holidays
Pet-friendly Holidays
Spa Holidays
Spa Holidays
Spa Holidays

Frequently asked questions

How much does a South Chicago holiday package cost?
Live it up in South Chicago from just . 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.
See properties

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$39
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

AU$35
per adult
90% 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

AU$58
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.