$51 Cheap flight deals from Hagerstown (DCA) to Chicago (CHI)

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This Weekend's Flight Deals from Hagerstown to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Jun 20 - Tue, Jun 24
IAD
Washington Dulles Intl.
MDW
Midway Intl.
$170 Roundtrip, found 2 hours ago
$170
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Fri, Jun 20 from Washington Dulles Intl. to Midway Intl., returning Tue, Jun 24, priced at $170 found 2 hours ago
Fri, Jun 20 - Tue, Jun 24
IAD
Washington Dulles Intl.
ORD
O'Hare Intl.
$190 Roundtrip, just found
$190
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Jun 20 from Washington Dulles Intl. to O'Hare Intl., returning Tue, Jun 24, priced at $190 just found
Sun, Jun 22 - Wed, Jun 25
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$287 Roundtrip, found 17 hours ago
$287
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Sun, Jun 22 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Wed, Jun 25, priced at $287 found 17 hours ago
Sat, Jun 21 - Tue, Jun 24
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$297 Roundtrip, just found
$297
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Jun 21 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Tue, Jun 24, priced at $297 just found

Airfares from $51 One Way, $100 Round Trip from Hagerstown to Chicago

Prices starting at $100 for return flights and $51 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Sep 4 - Sun, Sep 7
BWI
Baltimore
ORD
Chicago
$100 Roundtrip, found 1 hour ago
$100
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Thu, Sep 4 from Baltimore to Chicago, returning Sun, Sep 7, priced at $100 found 1 hour ago
Wed, Jul 9 - Wed, Jul 16
BWI
Baltimore
MDW
Chicago
$108 Roundtrip, found 6 hours ago
$108
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Wed, Jul 9 from Baltimore to Chicago, returning Wed, Jul 16, priced at $108 found 6 hours ago
Thu, Sep 4 - Sat, Sep 6
BWI
Baltimore
ORD
Chicago
$148 Roundtrip, found 11 hours ago
$148
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Thu, Sep 4 from Baltimore to Chicago, returning Sat, Sep 6, priced at $148 found 11 hours ago
Thu, Sep 4 - Sat, Sep 6
BWI
Baltimore
ORD
Chicago
$148 Roundtrip, found 11 hours ago
$148
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Thu, Sep 4 from Baltimore to Chicago, returning Sat, Sep 6, priced at $148 found 11 hours ago
Thu, Sep 25 - Tue, Sep 30
IAD
Washington
ORD
Chicago
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select United flight, departing Thu, Sep 25 from Washington to Chicago, returning Tue, Sep 30, priced at $157 found 1 day ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel
3.5-star property

Congress Plaza Hotel

8/10 Very Good! (8,858 reviews)

Aug 9 - Aug 14

5 night stay

Baltimore (BWI) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Baltimore (BWI)

Spirit Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
It’s was easy- we were in our rooms within a Few minutes of arriving

Reviewed on Jun 1, 2025

Bluegreen Vacations Hotel Blake, Ascend Resort Collection
4.0-star property

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

9.6/10 Exceptional! (1,004 reviews)

Aug 9 - Aug 14

5 night stay

Baltimore (BWI) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Baltimore (BWI)

Spirit Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Entire staff from front desk to security to housekeeping made us feel welcome and our stay comfortable. The central location allowed us to do a lot over our short weekend stay. Would not skip breakfast at the Meli cafe downstairs.

Reviewed on Feb 18, 2025

Embassy Suites by Hilton Chicago Downtown River North
4.0-star property

Embassy Suites by Hilton Chicago Downtown River North

8.4/10 Very Good! (4,196 reviews)

Aug 9 - Aug 14

5 night stay

Baltimore (BWI) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Baltimore (BWI)

Spirit Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Excellent stay. Room was clean and well-designed for our family. Fantastic complimentary breakfast every morning.

Reviewed on Jun 13, 2025

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More About Flying To Chicago from Hagerstown

Route Information for Flights from Hagerstown to Chicago

Origin Airport IATA Code
DCA
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Hagerstown to Chicago

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Use the Orbitz app or the mobile Orbitz site, m.orbtiz.com, to see information about your Hagerstown to Chicago flights anytime you need it. Your itinerary is also sent to your email address for reference. Access updates on your flights from Hagerstown to Chicago on your mobile device too, including delays and baggage claim details.

Cheap Air Ticket Prices Guaranteed

Orbitz is your number one source for low fares for Hagerstown to Chicago flights. Our low price guarantee on domestic and international air tickets give you great savings for a perfect trip to Chicago. Need hotels too? You can book them last minute on your mobile phone.

Frequently asked questions

Are there non-stop flights from Hagerstown to Chicago?
There certainly are, which is fantastic news if you’re not a huge fan of changing planes en route. United Airlines and American Airlines offer nonstop flights from National Airport to ORD.
What is the shortest flight from Hagerstown to Chicago?
The journey from Hagerstown to Chicago can be as quick as 2 hours and 43 minutes. With a short and sweet flight time like this, why not round up some friends and take off on an impromptu getaway?
What airlines fly from Hagerstown to Chicago most frequently?
Consider booking a flight with United Airlines (UA), which frequently services this route. This airline operates 208 flights each month between DCA and O’Hare Intl. Airport (ORD). American Airlines (AA) will also get you to your destination in style and comfort. Offering 199 flights every month between Hagerstown and Chicago, it’s another popular airline to look into.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won’t keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.