South Chicago Holidays

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    Save up to €185 when you book a flight and hotel together*
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Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Trump International Hotel & Tower Chicago
The Emily Hotel
Park Hyatt Chicago
Hotel Felix River North/Magnificent Mile

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

Top hotels in South Chicago

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €151 per night from 1 Sept to 2 Sept
€151
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,213 reviews)
Great hotel and location!
"Everything about the stay was awesome. The service, the guys handling the bags, the rooms, the custodians, the view from the balacony and gym. Especially the speed bag in the gym! I highly recommend this hotel, it was great to see the fireworks at Navy pier from the balacony as well."

Reviewed on 23 Aug 2025

The Wade
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €108 per night from 25 Aug to 26 Aug
€108
25 Aug - 26 Aug
includes taxes & fees
7.8/10 Good! (8,982 reviews)
"Experience what it must have felt like to attend the 1893 Worlds Fair"

Reviewed on 22 Aug 2025

Congress Plaza Hotel
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 €152 per night from 3 Sept to 4 Sept
€152
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,743 reviews)
"Great breakfast, good location."

Reviewed on 22 Aug 2025

Embassy Suites by Hilton Chicago Downtown River North
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 €792. 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.

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