Far Southeast Side Vacation Packages

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Top Far Southeast Side Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
so I gotta say The royal sonesta river north in particular is amazing it feels more like a hotel, it feels like a small community and all the staff and guest know each other. The front desk woman Gabby is amazing and dope as heck. Shaunda is a travel guide there, shes hilarious and gave us wonderful recommendations in the area. Antwonne is a dope Bellman great service and attitude. Every detail was perfect Jessenia apart of the housekeeping staff has such good attention to detail when it came to fixing up and cleaning the room everything was so organized and neat. Now to the room it couldn't have been more perfect they upgraded us to the luxury suite and it was beautiful (use the tub as much as you can)

Reviewed on Aug. 15, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
Peninsula is simply the best. Top notch service, amenities and everything in between.

Reviewed on Aug. 14, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug. 10, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,033 reviews)
Lovely rooms and staff very friendly and helpful.

Reviewed on Aug. 15, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
One of the best hotels. I will definitely stay here again.

Reviewed on Aug. 16, 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

Travelers enjoy South Deering for its churches and lake views. Consider checking out Harborside International Golf Center while you're in the area.

Find hotels in South Deering

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Far Southeast Side Hotel Deals

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 CA $186 per night from Sep 1 to Sep 2
CA $186
CA $218 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (8,916 reviews)
"Great views of the lake. Good location for museum campus and northerly island."

Reviewed on Aug. 14, 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 CA $222 per night from Sep 3 to Sep 4
CA $222
CA $261 total
Sep 3 - Sep 4
includes taxes & fees
8.4/10 Very Good! (4,711 reviews)
"Happy Hour drinks were amazing!"

Reviewed on Aug. 16, 2025

Embassy Suites by Hilton Chicago Downtown River North
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $240 per night from Sep 3 to Sep 4
CA $240
CA $316 total
Sep 3 - Sep 4
includes taxes & fees
8.4/10 Very Good! (1,856 reviews)
"Loved the Palmer House Hotel!!! The lobby, amazing decoration! I even took a picture of it to post on social. The bar and restaurant area, very popular and looked like everyone was enjoying themselves! The room, well, not the best, but this was an occasion where I booked last minute and through a ..."

Reviewed on Aug. 15, 2025

Palmer House a Hilton Hotel
See all 4,600 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.
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Discover the most popular places to visit in Far Southeast Side

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

Wrigley Field

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

Wrigley Field
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

You can enjoy some retail therapy 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
Navy Pier

Navy Pier

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

Navy Pier

What to do in Far Southeast Side

River tour boat in Chicago

Architecture River Tour

CA $57
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $62
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $56
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Far Southeast Side

Frequently asked questions

How much does a Far Southeast Side vacation package cost?
We make it easy to see the world, with Far Southeast Side vacation packages starting from as low as CA $681. 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 vacation 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 vacation?
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 vacation 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 vacation package is the most convenient way to organize 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 vacation 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 vacation 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 vacation 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.