Far Southeast Side Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Far Southeast Side Vacation Deals

Price found within the past 48 hours. Click for updated prices.
La Banque Hotel

La Banque Hotel

4 out of 5
Price was CA $1,112, price is now CA $835 per person
CA $835
per person
May 28 - May 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (473 reviews)
Room was amazing and beautiful and comfortable Only issue was when we arrived they had a plumbing issue and the whole place smelled horrific like a sewer. We didn’t go eat at the restaurant because the smell made us nauseous

Reviewed on Mar 1, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,978, price is now CA $1,326 per person
CA $1,326
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Great service, loved this place.

Reviewed on Apr 9, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $2,370, price is now CA $1,624 per person
CA $1,624
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
Breakfast was very good. Enjoyed our room and how everything was clean. There was no microwave so don’t try to bring food if you need to reheat it. Fridge was also not strong to freeze my ice cream so be aware. All the staff were kind and helpful. Rooftop was beautiful but the glass floor was out of service. The hotel was close to Michigan Ave so heading to stores was a breeze. Overall, had an amazing time with my partner and would recommend reserving a room at this establishment.

Reviewed on Apr 10, 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 $2,717, price is now CA $1,923 per person
CA $1,923
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Great place to stay

Reviewed on Apr 7, 2026

Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
Downtown Chicago
Price was CA $1,520, price is now CA $1,126 per person
CA $1,126
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (3,032 reviews)
Warwick Allerton is my favorite place to stay when visiting Chicago! Staying in the Gold Coast means walking distance from the restaurants, stores and other Chicago touristy things. Super close to Nordstrom, Tiffany, Ralph Lauren etc. 5 minute walk to Steak 48 for dinner & about a 15 minute walk to the Navy Pier! A Walgreens is also close by for any last minute needs or touristy things like magnets and keychains. This hotel was also very accommodating, clean and had super kind staff. Parking is simple.. either use valet at the hotel or the hotel next door’s parking garage!

Reviewed on Apr 7, 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?

 

Choose your dates

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 $159 per night from Apr 26 to Apr 27
CA $159
CA $187 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (10,076 reviews)
Room was clean, but cheaply remodeled and nothing really special.

Reviewed on Apr 9, 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 $189 per night from Apr 26 to Apr 27
CA $189
CA $222 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (4,089 reviews)
It was nice

Reviewed on Apr 10, 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 $215 per night from Apr 19 to Apr 20
CA $215
CA $252 total
Apr 19 - Apr 20
includes taxes & fees
8.6/10 Excellent! (5,828 reviews)
Perfect location for a family trip, the hotel amenities were amazing and the staff was very friendly. We did have an issue with having our room serviced during our stay, after a long day out we came back to it still not being serviced, after asking the front desk they said they would put in the request ...

Reviewed on Apr 9, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,735 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
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $61
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
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.

Explore a world of travel with Expedia

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