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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,455, price is now CA $997 per person
CA $997
per person
May 23 - May 27
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Yessss it’s was amazing

Reviewed on Apr 13, 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 CA $2,367, price is now CA $1,530 per person
CA $1,530
per person
Jun 1 - Jun 5
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Breakfast and parking not included

Reviewed on Apr 12, 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Price was CA $2,032, price is now CA $1,384 per person
CA $1,384
per person
Jun 1 - Jun 5
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Great location and converted old Virgin Hotel. Room was fine and hotel basics were fine. There wasn’t any room service daily or for my 3 night stay. There was a strike for housekeepers and they were LOUD out front everyday. Not sure what the hotel fee was for on top of Expedia hotel charge was for, they gave me 2 waters the first day and that was it. They also upsell their vacation club/time share a lot, kinda odd.

Reviewed on Apr 14, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,484, price is now CA $1,060 per person
CA $1,060
per person
Jul 3 - Jul 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (453 reviews)
This property never disappoints! The staff are awesome, particularly Nu at the front desk! Always very pleasant and friendly, provides awesome service every time we visit!

Reviewed on Apr 13, 2026

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was CA $2,434, price is now CA $1,746 per person
CA $1,746
per person
Jul 6 - Jul 10
found 9 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
The best hotel I've ever stayed in. Please get an iron, please get a microwave. And please don’t charge for every single thing! ❤️

Reviewed on Apr 13, 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

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

Ready to book your vacation to Far Southeast Side?

 

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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 $158 per night from Apr 26 to Apr 27
CA $158
CA $186 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (10,151 reviews)
It’s in a great location and the staff is always nice.

Reviewed on Apr 15, 2026

Congress Plaza Hotel
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 CA $188 per night from Apr 26 to Apr 27
CA $188
CA $221 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (4,125 reviews)
Loved the suite, connecting rooms! Needs a bit of renovating for rugs and wood! No room service!! Ok lobby.

Reviewed on Apr 15, 2026

Hilton Chicago/Magnificent Mile Suites
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 $213 per night from Apr 29 to Apr 30
CA $213
CA $250 total
Apr 29 - Apr 30
includes taxes & fees
8.6/10 Excellent! (5,840 reviews)
Room was hot , we were 6 not enough of towels breakfast good staff were great

Reviewed on Apr 15, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,696 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.
All Inclusive Vacations
All Inclusive Vacations
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Discover the most popular places to visit in Far Southeast Side

Wrigley Field

Wrigley Field

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
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.