Far Southeast Side Holidays
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Top Flight + Hotel Deals in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
€1,528
per person
3 Oct - 7 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,654 reviews)
My stay was amazing, the view was spectacular- a self contained, day date to treat myself to the sites, sounds & view of Sweet Home Chicago! I booked a return visit for December before breakfast 😂
Reviewed on 30 Aug 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
€1,406
per person
3 Oct - 7 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,853 reviews)
The room was good enough and as advertised. Had multiple billing issues which were stressful, and the hotel hosted a wedding one night we were there and our room was literally shaking until the event ended. The view from our upgraded river room suite was also much worse than we expected because of the hotel across the river.
Overall it was a reasonably nice hotel but I would not stay there again.
Reviewed on 30 Aug 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
€1,755
per person
3 Oct - 7 Oct
found 19 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,986 reviews)
Everything was excellent. Very clean. Staff members all very nice! Our view was the best!
Reviewed on 30 Aug 2026
Where to stay in Far Southeast Side
Find the best Far Southeast Side areas and neighborhoods for the activities you enjoy most. Learn more about Far Southeast Side
South Chicago
1 out of top 10 points of interest in this area
You'll enjoy the beaches and restaurants in South Chicago. You might want to make time for a stop at Lake Michigan or Mahalia Jackson Residence.
South Deering
1 out of top 10 points of interest in this area
Visitors to South Deering like its churches and lake views, and Harborside International Golf Center is a sight worth a stop.
Roseland
3 out of top 10 points of interest in this area
Well liked for its restaurants and parks, Roseland is worth a visit. Check out the variety of things to see and do like Chicago State University and Jones Convocation Center, and jump on the metro at 95th-Dan Ryan Station to get around the city.
Chatham
The beaches and restaurants make Chatham worth a stop. Make a stop by Johnson Products, and jump on the metro at 87th Station to get around the area.
Calumet Heights
1 out of top 10 points of interest in this area
Visitors to Calumet Heights like its beaches and restaurants, and Bronzeville Children's Museum is a sight worth a stop.
Top hotels in Far Southeast Side
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
€118
8 Sept - 9 Sept
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
€137
31 Aug - 1 Sept
includes taxes & fees
8/10 Very good! (2,125 reviews)
"Staff were amazing! Extremely helpful and accommodating, let us check in about 5 hours early. Definitely recommend"
Reviewed on 29 Aug 2026
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
9.4/10 Exceptional! (880 reviews)
"Check in can be slightly confusing however you get the hang of it quickly. It was close to many amenities, a train away or a longer walk. The loft was cleaning than most however there was still dust and some crumbs left behind. Over all we were pleased with our stay even though very pricey for 3 ..."
Reviewed on 29 Aug 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.
Stay near popular Far Southeast Side attractions
Harborside International Golf Center
Enjoy a round of golf in Chicago at Harborside International Golf Center. Stroll along the lakeside or attend a sporting event in this vibrant area.
Abbott Park
Abbott Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its acclaimed art galleries.
Chicago State University
Explore the campus of Chicago State University as part of your travels around Chicago. Amble around the area's parks or visit its shops.
A. Philip Randolph Pullman Porter Museum
You can spend time studying the exhibits at A. Philip Randolph Pullman Porter Museum in Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.
Pullman Historic District
Find out about the history of Chicago when you take a trip to Pullman Historic District. Take in the museums while you're in the area.
William W. Powers State Recreation Area
You can take time to visit William W. Powers State Recreation Area during your travels to Chicago.
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.
Pullman Community Center
Enjoy an outing to Pullman Community Center during your stay in Chicago. Take in the museums while you're in the area.
What to do in Far Southeast Side
Chicago: Navy Pier Centennial Wheel Ticket
€21
per adult
90% of travellers recommend
Frequently asked questions
How much does a Far Southeast Side holiday package cost?
We make it easy to see the world, with Far Southeast Side holiday packages starting from as low as €1,058. You'll have the flexibility to combine your preferred airlines, hotels and car rental. For the ultimate getaway, why not add a couple of tours and activities to your itinerary?
How do I get a cheap travel package to Far Southeast Side?
Combine your hotel and flight bookings, add extras such as a rental car or activities, and save with a Far Southeast Side holiday package. You won't just enjoy impressive discounts on your getaway — you'll have loads of choice at your fingertips too. When you book with Expedia, you can select from more than 550 partner airlines and 1,000,000 properties throughout the world. Your next grand adventure begins right here, right now!
What are the top hotels in Far Southeast Side?
When it comes to properties in Chatham Fields, Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton are two terrific options. If you're heading to Cheltenham, The Whitehall Hotel and Hyatt Regency Chicago will make you feel right at home.
How far in advance should I book my Far Southeast Side holiday?
It's hard to pick the perfect time for airfares, but we normally say the earlier, the better. Most international flights on Expedia become available up to 12 months in advance. If you're booking late, don't worry. Cheap prices appear from time to time just weeks before departure dates.
What does an Expedia Far Southeast Side travel package include?
It comes down to what type of trip you have in the works. Far Southeast Side holiday deals can include car rentals, hotels and flights. You can mix and match to create the bundle that suits your needs. You can also add on experiences and activities after you've booked to pick up even bigger discounts.
What should I know before booking a Far Southeast Side travel package?
Bundling your bookings into a Far Southeast Side holiday package is the most convenient way to organise your trip. Not only that, you'll save just for combining your hotels, flights and car rentals. Once you've booked, why not add on a tour or an activity?
Can I choose my airline with a Far Southeast Side Expedia holiday package?
Most definitely. Expedia has more than 550 airline partners to choose from worldwide. With such a big range of choice, finding the perfect carrier to whisk you off to Far Southeast Side won't be hard.
If I'm not able to travel, can I cancel my Far Southeast Side holiday package?
You can. We get that even the best-laid plans can fail, so we're happy to help if you have to make changes to your Far Southeast Side holiday package. It may be possible to cancel or amend your itinerary for free if you've booked within 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Have a look at our Customer Service Portal for further information. Also, be sure to check your itinerary for the nitty-gritty on change fees.
Explore a world of travel with Expedia
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- Aon Center
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- Buckingham Fountain
- Canalport Riverwalk Park
- Chicago Board of Trade Building
- Visit Calumet Heights
- Visit Canaryville
- Visit Dixmoor
- Chicago Museum Campus Holidays
- Chicago Place Mall
- Visit Pullman
- Chicago Riverwalk
- Visit Roseland
- Visit Washington Park
- Visit West Pullman
- Chicago Holidays
- Cloud Gate
- Credit Union 1 Arena
- Crown Fountain
- Daley Plaza
- Grant Park
- Hometown Holidays
- Hyde Park Hair Salon
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- Lake Meadows Park
- Millennium Park
- Navy Pier
- Newberry Library
- Visit Oak Lawn
- Prentice Women's Hospital
- Riverdale Holidays
- Visit Riverdale
- Robie House
- Second Franklin Building
- Visit South Holland
- University of Illinois Chicago
- Willis Tower
- Wrigley Building
- Car hire near Chicago
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- Car hire near Gaelic Park
- Car hire Harvey
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- Car hire Oak Lawn
- Car hire near West Pullman
- Enterprise Rental Cars in North Pullman
- Europcar Rental Cars in Far Southeast Side
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- Hertz Rental Cars in West Harvey
- National Car Rental Rental Cars in Far Southeast Side
- Sixt Rental Cars in Far Southeast Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
