South Chicago Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 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
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was €1,364, price is now €1,012 per person
€1,012
per person
24 Jul - 27 Jul
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
the only issue i had it was that they didn’t do room service in the room, no new towels , no toilet paper and stuff like that

Reviewed on 12 Jun 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was €1,658, price is now €1,228 per person
€1,228
per person
24 Jul - 28 Jul
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (491 reviews)
Great place near the fun spots

Reviewed on 12 Jun 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was €1,486, price is now €1,170 per person
€1,170
per person
24 Jul - 27 Jul
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
This is our second time staying at the sable and it was wonderful! The staff is amazing and friendly! The elevators were out and we got lost a couple times getting to our room, and every single staff member that we would run into each time was so helpful and kind in finding where we were supposed to go! One of the housekeepers even stopped what she was doing to walk us to our correct floor when she realized we were lost! She was so incredibly nice! The views are incredible, the location is incredible, and the staff is incredible! Will definitely be coming back on our next trip to Chicago/Navy Pier!

Reviewed on 11 Jun 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was €1,518, price is now €1,221 per person
€1,221
per person
24 Jul - 27 Jul
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,119 reviews)
Great staff and property!

Reviewed on 10 Jun 2026

Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was €1,303, price is now €1,070 per person
€1,070
per person
24 Jul - 27 Jul
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (2,134 reviews)
Lovely stay no complaints

Reviewed on 11 Jun 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

Downtown Chicago

5 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

Top hotels in South Chicago

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 €140 per night from 30 Jun to 1 Jul
€140
30 Jun - 1 Jul
includes taxes & fees
8/10 Very Good! (10,256 reviews)
"Had to shut refrigerator off because when running the noise was loud. Restaurant had little staffing and therefore very slow. Fifthteen minutes to get service and cup of coffee."

Reviewed on 13 Jun 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is €148 per night from 30 Jun to 1 Jul
€148
30 Jun - 1 Jul
includes taxes & fees
7.8/10 Good! (1,569 reviews)
"I"

Reviewed on 12 Jun 2026

The Chicago Hotel Collection - Magnificent Mile
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is €161 per night from 29 Jun to 30 Jun
€161
29 Jun - 30 Jun
includes taxes & fees
8.2/10 Very Good! (1,599 reviews)
"Very easy check in. Very clean. Staff were very helpful. Beds are super comfortable. Parking little hard, but across the street on corner there's a lot for 58 dollars overnight a s hotel charges 80 dollars a night."

Reviewed on 13 Jun 2026

The Chicago Hotel Collection Ambassador Gold Coast
See all 4,334 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.

Frequently asked questions

How much does a South Chicago holiday package cost?
Live it up in South Chicago from just €1,012. 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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.