Far Southeast Side Holidays

Photo by Marc Jacobs

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Top Flight + Hotel Deals in Far Southeast Side

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
21 Aug - 26 Aug
found 1 day ago
Return direct flight included
Warsaw (WAW) to Chicago (ORD)
8.8/10 Excellent! (1,796 reviews)
It’s an older hotel with some charm the cold eucalyptus towel in the gym was the best part of my stay. It is close to restaurants shopping and theaters. The AC work but not super cold

Reviewed on 14 Jul 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
21 Aug - 26 Aug
found 1 day ago
Return direct flight included
Warsaw (WAW) to Chicago (ORD)
9.2/10 Wonderful! (1,769 reviews)
It’s not what I was expecting, I was expecting something different , no views, not happy at all

Reviewed on 14 Jul 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
21 Aug - 26 Aug
found 1 day ago
Return direct flight included
Warsaw (WAW) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I loved the location of the property, and the overall concept of something fun and funky, but I had a "higher end" room, and it was right near the elevator, so I got a lot of noise on that side, plus the El from the other side. The rug wasn't super clean (although the bedding and the rest of the room were a delight). The most annoying thing was the TV. Anything I turned it to, 10 minutes later to the minute, it went back to the Virgin channel #1, here are all our hotels in the world. I really hated having to stay on top of a show, when usually I want the tv on as background while I'm getting ready, etc. Also, this hotel's amenities were oversold, i.e., good luck getting on the rooftop, especially if you just wanted a quiet sip of a drink. I loved the cafe and the staff, though, everyone was very pleasant.

Reviewed on 15 Jul 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
21 Aug - 26 Aug
found 1 day ago
Return direct flight included
Warsaw (WAW) to Chicago (ORD)
9.2/10 Wonderful! (1,115 reviews)
Spacious room with a very comfortable bed, comfortable room temperature on a hot weekend, large bathroom and spacious work station. Close to trains that transport to the loop within minutes.

Reviewed on 8 Jul 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
per person
21 Aug - 26 Aug
found 1 day ago
Return direct flight included
Warsaw (WAW) to Chicago (ORD)
9/10 Wonderful! (1,000 reviews)
Nice room and view. Rooftop was gorgeous

Reviewed on 13 Jul 2025

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
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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.

Find hotels in South Deering

Top hotels in Far Southeast Side

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 €178 per night from 4 Aug to 5 Aug
€178
4 Aug - 5 Aug
includes taxes & fees
7.8/10 Good! (8,961 reviews)
"Convenient location & very friendly & helpful staff!"

Reviewed on 13 Jul 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is €227 per night from 10 Aug to 11 Aug
€227
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (2,039 reviews)
"I truly enjoyed my stay at this hotel. The staff was splendid!"

Reviewed on 14 Jul 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €149 per night from 10 Aug to 11 Aug
€149
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (2,429 reviews)
"I always prefer staying in Hilton!"

Reviewed on 12 Jul 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,468 properties in Far Southeast Side
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.

Popular places to visit

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Navy Pier

Navy Pier

4/5(125 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Magnificent Mile - River North showing street scenes, signage and night scenes

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue

What to do in Far Southeast Side

River tour boat in Chicago

Architecture River Tour

€41
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

€38
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

€38
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Far Southeast Side

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 €785. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.