$253+ Cheap flights from Salisbury, MD (SBY) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
SBY — CHI
Sep 20 — Sep 271
Round-trip
1 adult, Economy
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Find cheap flights from Salisbury to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Salisbury to Chicago
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One-way
Cheapest flights from Salisbury to ChicagoExplore 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 August 21, 2026.
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 August 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 9/188:35 pm -
2 stops22h 52m
Fri 9/2511:15 am -
1 stop7h 16m
Deal found 8/20![Multiple Airlines logo]()
$408
This American Airlines deal was found by Cheapflights users on 8/18. 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 10/16:00 am -
1 stop7h 14m
Sat 10/34:00 pm -
1 stop5h 59m
Deal found 8/18![American Airlines logo]()
$530
This American Airlines deal was found by Cheapflights users on 8/21. 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 9/56:05 am -
1 stop5h 46m
Wed 9/96:29 am -
1 stop4h 52m
Deal found 8/21![American Airlines logo]()
$583
This American Airlines deal was found by Cheapflights users on 8/16. 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 9/112:35 pm -
1 stop6h 07m
Sat 9/53:25 pm -
1 stop4h 33m
Deal found 8/16![American Airlines logo]()
$586
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Wed 8/198:06 pm -
1 stop17h 44m
Thu 8/207:44 pm -
1 stop23h 10m
Deal found 8/16![Multiple Airlines logo]()
$590
This American Airlines deal was found by Cheapflights users on 8/19. 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.
Wed 9/98:45 am -
1 stop6h 24m
Sun 9/135:48 pm -
1 stop4h 11m
Deal found 8/19![American Airlines logo]()
$630
This American Airlines deal was found by Cheapflights users on 8/20. 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.
Sun 8/306:41 am -
1 stop5h 27m
Sat 9/511:53 am -
1 stop7h 03m
Deal found 8/20![American Airlines logo]()
$633
This American Airlines deal was found by Cheapflights users on 8/17. 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.
Mon 9/146:41 am -
1 stop6h 35m
Sat 9/193:00 pm -
1 stop6h 59m
Deal found 8/17![American Airlines logo]()
$857
Best flights from Salisbury to ChicagoDiscover carefully curated flight deals from Salisbury to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
Discover carefully curated flight deals from Salisbury to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 9/188:35 pm -
2 stops22h 52m
Fri 9/2511:15 am -
1 stop7h 16m
Deal found 8/20![Multiple Airlines logo]()
$408
This American Airlines deal was found by Cheapflights users on 8/21. 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 9/56:05 am -
1 stop5h 46m
Wed 9/96:29 am -
1 stop4h 52m
Deal found 8/21![American Airlines logo]()
$583
This American Airlines deal was found by Cheapflights users on 8/16. 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 9/112:35 pm -
1 stop6h 07m
Sat 9/53:25 pm -
1 stop4h 33m
Deal found 8/16![American Airlines logo]()
$586
This American Airlines deal was found by Cheapflights users on 8/19. 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.
Wed 9/98:45 am -
1 stop6h 24m
Sun 9/135:48 pm -
1 stop4h 11m
Deal found 8/19![American Airlines logo]()
$630
This American Airlines deal was found by Cheapflights users on 8/20. 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 9/412:35 pm -
1 stop5h 13m
Tue 9/85:05 pm -
1 stop4h 53m
Deal found 8/20![American Airlines logo]()
$633
This American Airlines deal was found by Cheapflights users on 8/17. 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.
Mon 9/146:41 am -
1 stop6h 35m
Sat 9/193:00 pm -
1 stop6h 59m
Deal found 8/17![American Airlines logo]()
$857
This American Airlines deal was found by Cheapflights users on 8/18. 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 10/16:41 am -
2 stops6h 55m
Sat 10/35:48 pm -
1 stop4h 11m
Deal found 8/18![American Airlines logo]()
$945
Last-minute flights from Salisbury to ChicagoDiscover last-minute flight deals from Salisbury to Chicago. Data last updated August 21, 2026 and is based on user searches.
Discover last-minute flight deals from Salisbury to Chicago. Data last updated August 21, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/20. 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.
Sun 8/306:41 am -
1 stop5h 27m
Sat 9/511:53 am -
1 stop7h 03m
Deal found 8/20![American Airlines logo]()
$633
This American Airlines deal was found by Cheapflights users on 8/16. 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 9/112:35 pm -
1 stop6h 07m
Sat 9/53:25 pm -
1 stop4h 33m
Deal found 8/16![American Airlines logo]()
$586
This American Airlines deal was found by Cheapflights users on 8/20. 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 9/412:35 pm -
1 stop5h 13m
Tue 9/81:19 pm -
2 stops5h 52m
Deal found 8/20![American Airlines logo]()
$912
This American Airlines deal was found by Cheapflights users on 8/21. 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 9/56:05 am -
1 stop5h 46m
Wed 9/96:29 am -
1 stop4h 52m
Deal found 8/21![American Airlines logo]()
$583
This American Airlines deal was found by Cheapflights users on 8/19. 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.
Wed 9/98:45 am -
1 stop6h 24m
Sun 9/135:48 pm -
1 stop4h 11m
Deal found 8/19![American Airlines logo]()
$630
This American Airlines deal was found by Cheapflights users on 8/17. 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.
Mon 9/146:41 am -
1 stop6h 35m
Sat 9/193:00 pm -
1 stop6h 59m
Deal found 8/17![American Airlines logo]()
$857
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 9/188:35 pm -
2 stops22h 52m
Fri 9/2511:15 am -
1 stop7h 16m
Deal found 8/20![Multiple Airlines logo]()
$408
One-way flights from Salisbury to ChicagoSearch for one-way flight options from Salisbury to Chicago. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
Search for one-way flight options from Salisbury to Chicago. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Wed 9/29:12 pm -
1 stop26h 56m
Deal found 8/17![Multiple Airlines logo]()
$253
This KAYAK deal was found by Cheapflights users on 8/19. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:35 pm -
1 stop6h 07m
Deal found 8/19![American Airlines logo]()
$488
Find 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 August 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $408 (Kiwi.com) |
One-way from | $253 (Kiwi.com) |
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 7,457,451 searches. Data last updated August 21, 2026.
Use the filters below to find and compare flights from Salisbury to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
SalisburyChicago
SBY Salisbury-Ocean City - ORD Chicago O'Hare Intl
SBYORD
Salisbury-Ocean City
Fri 9/18
8:35 pm-6:27 pm
2 stops22h 52m
Chicago O'Hare Intl
Fri 9/25
11:15 am-7:31 pm
1 stop7h 16m
$408
SalisburyChicago
SBY Salisbury-Ocean City - ORD Chicago O'Hare Intl
SBYORD
Salisbury-Ocean City
Sat 9/5
6:05 am-10:51 am
1 stop5h 46m
Chicago O'Hare Intl
Wed 9/9
6:29 am-12:21 pm
1 stop4h 52m
$583
SalisburyChicago
SBY Salisbury-Ocean City - ORD Chicago O'Hare Intl
SBYORD
Salisbury-Ocean City
Tue 9/1
12:35 pm-5:42 pm
1 stop6h 07m
Chicago O'Hare Intl
Sat 9/5
3:25 pm-8:58 pm
1 stop4h 33m
$586
SalisburyChicago
SBY Salisbury-Ocean City - ORD Chicago O'Hare Intl
SBYORD
Salisbury-Ocean City
Wed 9/9
8:45 am-2:09 pm
1 stop6h 24m
Chicago O'Hare Intl
Sun 9/13
5:48 pm-10:59 pm
1 stop4h 11m
$630
Quickest round-trip
SalisburyChicago
SBY Salisbury-Ocean City - ORD Chicago O'Hare Intl
SBYORD
Salisbury-Ocean City
Fri 9/4
12:35 pm-4:48 pm
1 stop5h 13m
Chicago O'Hare Intl
Tue 9/8
5:05 pm-10:58 pm
1 stop4h 53m
$633
SalisburyChicago
SBY Salisbury-Ocean City - ORD Chicago O'Hare Intl
SBYORD
Salisbury-Ocean City
Mon 9/14
6:41 am-12:16 pm
1 stop6h 35m
Chicago O'Hare Intl
Sat 9/19
3:00 pm-10:59 pm
1 stop6h 59m
$857
SalisburyChicago
SBY Salisbury-Ocean City - ORD Chicago O'Hare Intl
SBYORD
Salisbury-Ocean City
Thu 10/1
6:41 am-12:36 pm
2 stops6h 55m
Chicago O'Hare Intl
Sat 10/3
5:48 pm-10:59 pm
1 stop4h 11m
$945
Cheapest one-way
SalisburyChicago
SBY Salisbury-Ocean City - ORD Chicago O'Hare Intl
SBYORD
Salisbury-Ocean City
Wed 9/2
9:12 pm-7:12 pm
2 stops23h 00m
$254
Quickest one-way
SalisburyChicago
SBY Salisbury-Ocean City - ORD Chicago O'Hare Intl
SBYORD
Salisbury-Ocean City
Thu 8/27
12:35 pm-5:42 pm
1 stop6h 07m
$488
Sorted by cheapest first
Compare providers for flights from Salisbury to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Salisbury to Chicago in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Salisbury, Maryland-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Salisbury, Maryland-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Salisbury, Maryland-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Salisbury, Maryland-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Salisbury, Maryland-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
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.
SBY-CHI
SBY-ORD
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
SBY-CHI
SBY-ORD
No data available for this route at this time. Please check back soon.
Related info for your journey
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Traveling to a place near Chicago?
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