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$280+ Cheap flights from Salisbury, MD (SBY) to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
SBY — CHI
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Salisbury to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Salisbury (SBY) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 16, 2025.

Round-trip from

$280
(Kiwi.com)
From Salisbury-Ocean City to Chicago (CHI)
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Find flight deals from Salisbury to Chicago

Cheapest flights from Salisbury to Chicago
Explore the most affordable flight options available from Salisbury to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/78:02 pmSBY - ORD
1 stop20h 06mMultiple Airlines
Mon 11/105:15 amORD - SBY
1 stop13h 07mMultiple Airlines
Deal found 9/14$280
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/305:44 pmSBY - ORD
1 stop6h 10mAmerican Airlines
Sun 11/211:20 amORD - SBY
1 stop6h 13mAmerican Airlines
Deal found 9/14$470
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/278:45 amSBY - ORD
1 stop6h 21mAmerican Airlines
Tue 9/308:35 amORD - SBY
1 stop6h 59mAmerican Airlines
Deal found 9/14$476
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/185:00 amSBY - ORD
1 stop5h 25mAmerican Airlines
Sat 9/207:02 amORD - SBY
1 stop4h 45mAmerican Airlines
Deal found 9/14$548
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/304:07 pmSBY - ORD
1 stop5h 20mAmerican Airlines
Sat 10/412:33 pmORD - SBY
1 stop5h 51mAmerican Airlines
Deal found 9/15$645
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:00 amSBY - ORD
2 stops7h 25mAmerican Airlines
Sun 12/72:42 pmORD - SBY
1 stop4h 52mAmerican Airlines
Deal found 9/15$809

Cheapflights Fare Finder

 
Customize your flight search to find flights from Salisbury to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 16, 2025.
Use the filters below to find and compare flights from Salisbury to Chicago that are best for you.

Fly from

Salisbury

Fly to

Chicago

Route

Depart

Return

Price

SalisburyChicago

SBY - ORD

SBYORD

Salisbury-Ocean City

Fri 11/7

8:02 pm-3:08 pm

1 stop20h 06m

Chicago O'Hare Intl

Mon 11/10

5:15 am-7:22 pm

1 stop13h 07m

$280

SalisburyChicago

SBY - ORD

SBYORD

Salisbury-Ocean City

Fri 12/5

9:34 am-4:02 pm

1 stop7h 28m

Chicago O'Hare Intl

Sun 12/7

2:42 pm-8:34 pm

1 stop4h 52m

$470

SalisburyChicago

SBY - ORD

SBYORD

Salisbury-Ocean City

Thu 10/30

5:44 pm-10:54 pm

1 stop6h 10m

Chicago O'Hare Intl

Sun 11/2

11:20 am-6:33 pm

1 stop6h 13m

$470

SalisburyChicago

SBY - ORD

SBYORD

Salisbury-Ocean City

Sat 9/27

8:45 am-2:06 pm

1 stop6h 21m

Chicago O'Hare Intl

Tue 9/30

8:35 am-4:34 pm

1 stop6h 59m

$476

SalisburyChicago

SBY - ORD

SBYORD

Salisbury-Ocean City

Wed 3/11

12:11 pm-5:57 pm

1 stop6h 46m

Chicago O'Hare Intl

Sat 3/14

5:00 am-10:43 am

1 stop4h 43m

$530

SalisburyChicago

SBY - ORD

SBYORD

Salisbury-Ocean City

Tue 9/30

4:07 pm-8:27 pm

1 stop5h 20m

Chicago O'Hare Intl

Sat 10/4

12:33 pm-7:24 pm

1 stop5h 51m

$645

SalisburyChicago

SBY - ORD

SBYORD

Salisbury-Ocean City

Tue 11/11

6:30 am-10:25 am

1 stop4h 55m

$421

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Best time to book a flight from Salisbury to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Salisbury with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Salisbury to Chicago

What is the cheapest month to book a flight from Salisbury, Maryland to Chicago?

Currently, August is the cheapest month in which you can book a flight from Salisbury, Maryland to Chicago (average of $245). Flying from Salisbury, Maryland to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Salisbury to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Salisbury to Chicago?

    If you book a flight to Chicago from Salisbury, you will be flying from Salisbury-Ocean City, which is the city’s only airport. Salisbury-Ocean City (SBY) is located 5.0 mi from the center of Salisbury. There are 0 flights from Salisbury-Ocean City to Chicago per day from 0 different airlines.

  • How long is the flight from Salisbury, Maryland to Chicago?

    A quick flight from Salisbury, Maryland to Chicago can take about 7h 28m. American Airlines provides one of the quickest options available for as low as $470. Salisbury, Maryland and Chicago are separated by a distance of 700 mi.

  • Can I find deals for flights from Salisbury to Chicago that include hotel bookings?

    Yes. In addition to deals on Salisbury to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Salisbury to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Salisbury to Chicago.

  • Can I find deals for business class flights from Salisbury to Chicago?

    Yes. Cheapflights offers flight deals from Salisbury to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Salisbury, Maryland to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Salisbury, Maryland to Chicago (average of $245). Flying from Salisbury, Maryland to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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