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.
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
East Hazel Crest
Price was CA $1,073, price is now CA $806 per person
CA $806
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (MDW)
9.4/10 Exceptional! (160 reviews)
Yes, and friendly staff

Reviewed on Feb 27, 2026

La Banque Hotel

La Banque Hotel

4 out of 5
Price was CA $1,403, price is now CA $852 per person
CA $852
per person
Apr 23 - Apr 28
found 8 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.

Reviewed on Jan 26, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,994, price is now CA $1,286 per person
CA $1,286
per person
May 14 - May 18
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.

Reviewed on Feb 16, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,751, price is now CA $1,218 per person
CA $1,218
per person
Apr 22 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great breakfast and friendly staff

Reviewed on Feb 28, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $1,953, price is now CA $1,478 per person
CA $1,478
per person
Apr 23 - Apr 26
found 16 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Room was amazing. Staff was fantastic. Best Hotel we have ever stayed at

Reviewed on Feb 26, 2026

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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

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.

Find hotels in South Chicago

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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 $132 per night from Mar 2 to Mar 3
CA $132
CA $155 total
Mar 2 - Mar 3
includes taxes & fees
8/10 Very Good! (9,895 reviews)
We mainly go to Chicago for medical appointments and it is *so awesome* that you can actually open the windows here.That is the main reason we chose it. Because Dad has cancer we aired it out and then ran our own air purifier. No bad smells or anything, we're just being cautious because of his health. ...

Reviewed on Feb 27, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Mar 4 to Mar 5
CA $154
CA $219 total
Mar 4 - Mar 5
includes taxes & fees
9.4/10 Exceptional! (3,428 reviews)
Great breakfast and friendly staff

Reviewed on Feb 28, 2026

Hotel Riu Plaza Chicago
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 $151 per night from Mar 5 to Mar 6
CA $151
CA $177 total
Mar 5 - Mar 6
includes taxes & fees
8.6/10 Excellent! (5,698 reviews)
The room was clean but phone was left in room even thought no land line. Curtain hooks were not properly functioning. Being near casino, we were a little crowded and full of all kinds of people and a tad noisy. All and all it was decent place for a one night stay. Also, no complimentary water or ...

Reviewed on Mar 1, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,772 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
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

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 featuring a sunset and rides

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

Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $55
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $47
per adult
96% of travellers recommend
Color Factory Chicago Ticket
See all activities in Far Southeast Side

Frequently asked questions

Can I cancel my flight booking to Far Southeast Side due to COVID-19?
Head to our Customer Service Portal for important info about changing or canceling flights due to COVID-19. Make sure you also scan through the terms and conditions of your chosen carrier before you book your seat.
What's the best way to find cheap flights to Far Southeast Side that have flexible change policies?
At Expedia, we've been channeling our inner contortionist to provide you with the most flexible fares around. Simply mark the "No change fee" box directly underneath the "Flexible change policies" subheading to find the best flights to Far Southeast Side.
What are some of the general tips for travelers to Far Southeast Side during the COVID-19 outbreak?
The COVID-19 outbreak has transformed the world in a profound way, including how we can travel safely. The following tips will help you better understand the new challenges and prepare you for your flight to Far Southeast Side:
  • Before locking in your flight, find out if any travel restrictions or bans apply — in both your origin and destination. Stay informed with the latest updates by reviewing government websites.
  • Requirements state that you must wear a face mask at the airport, including at security checkpoints. You should be prepared to adjust your mask for identification purposes when asked by a TSA officer.
  • To reduce the possibility of cross-contamination, position your boarding pass on the scanner yourself and then hold it up for inspection. Do not hand your boarding pass directly to a TSA employee.
  • TSA is now permitting passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on luggage. This will need to be removed from your bag for screening.
  • Remove items from your pocket, such as your small change and phone, and place them in your carry-on instead of into bins. This will minimize handling during screening.
  • Transport any food items in a clear plastic bag and also place them in a screening bin. Separating food from your carry-on means it's less likely a TSA employee will need to touch and open your bag for inspection.

Which airlines fly to Far Southeast Side?
Organize your airfare with American Airlines and then start organizing your Far Southeast Side travel agenda. This leading airline offers 13307 flights every month to O'Hare Intl. Airport (ORD), a main gateway.
How can I find cheap tickets to Far Southeast Side?
You'll always find an unbeatable deal with Expedia, but our "flexible dates" feature makes it that much easier. Enter your preferred flight date, then check the flexible dates box above to see the cheapest prices for nearby days. was the cheapest price for a flight to Far Southeast Side in the last seven days.
How much is a flight to Far Southeast Side?
One-way trips departing from () sold for as little as in the last seven days. During this period, the cost of a return airfare to Far Southeast Side varied between and . If you find a deal, book as fast as you can — these prices don't stick around for long.
What are the most popular airports to fly into in Far Southeast Side?
Jet into O'Hare Intl. Airport (ORD) and experience everything that Far Southeast Side has to offer. As the region's main point of entry, roughly 33491 flights touch down here each month.
When is the cheapest time to fly to Far Southeast Side?
Fly out on a Tuesday to improve your chances of landing the cheapest fare to Far Southeast Side. Mondays are usually the second most affordable day to take off. Saturday is typically the costliest day to fly anywhere.
How much is a plane ticket to Far Southeast Side?
In the last seven days, plane fares varied between and . Check out our unbeatable deals to Far Southeast Side, make a booking and then get packing!
Which airlines with flights to Far Southeast Side employ COVID-19 cleanliness policies?
In response to the global COVID-19 pandemic, most airlines have adopted new precautionary measures to help passengers fly with confidence. Here are some good examples:
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.

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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.