Far Southeast Side Holidays from £504

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Top Far Southeast Side Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £747, price is now £504 per person
£504
per person
18 Jun - 21 Jun
found 4 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
8.2/10 Very Good! (2,636 reviews)
Kind staff and helpful, nice rooms, wish there was a fridge in the room.

Reviewed on 27 Apr 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £788, price is now £507 per person
£507
per person
18 Jun - 21 Jun
found 4 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Corner room with breath taking view. It was my second time in this hotel, it never disappoints.

Reviewed on 27 Apr 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
Save 100% on your flight
Price was £1,000, price is now £671 per person
£671
per person
18 Jun - 21 Jun
found 4 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
Great week-long stay. We loved the king corner room - the views were fantastic. Room was large and comfortable. All staff were really accommodating.

Reviewed on 29 Apr 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,205, price is now £840 per person
£840
per person
18 Jun - 21 Jun
found 4 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (1,851 reviews)
Absolutely fantastic will be back

Reviewed on 27 Apr 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £859, price is now £620 per person
£620
per person
18 Jun - 21 Jun
found 4 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (1,330 reviews)
Very nice property, good location, would stay here again.

Reviewed on 30 Apr 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

Far Southeast Side Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)

Top hotels in Far Southeast Side

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is £99 per night from 25 May to 26 May
£99
25 May - 26 May
includes taxes & fees
8.2/10 Very Good! (2,650 reviews)
Clean room

Reviewed on 30 Apr 2026

Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is £118 per night from 26 May to 27 May
£118
26 May - 27 May
includes taxes & fees
8.8/10 Excellent! (5,138 reviews)
Beautiful, clean room with an incredible downtown Chicago view. Totally worth it

Reviewed on 29 Apr 2026

River Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
Fully refundable
The price is £96 per night from 25 May to 26 May
£96
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (3,463 reviews)
Great check in and check out experience

Reviewed on 29 Apr 2026

Club Quarters Hotel, Central Loop, Chicago
See all 4,670 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

Wrigley Field

Wrigley Field

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

Wrigley Field
Navy Pier

Navy Pier

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

Navy Pier
Millennium Park

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park

What to do in Far Southeast Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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 cancelling 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 travellers 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?
Organise your airfare with American Airlines and then start organising 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. Flight-inclusive packages are ATOL protected.