$29 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, Dec 26 - Sat, Jan 10
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$309 Roundtrip, found 1 day ago
$309
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Dec 26 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Sat, Jan 10, priced at $309 found 1 day ago
Fri, Dec 26 - Tue, Dec 30
IAD
Washington Dulles Intl.
MDW
Midway Intl.
$359 Roundtrip, found 2 days ago
$359
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Dec 26 from Washington Dulles Intl. to Midway Intl., returning Tue, Dec 30, priced at $359 found 2 days ago
Sun, Dec 28 - Fri, Jan 2
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$390 Roundtrip, found 4 hours ago
$390
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sun, Dec 28 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Fri, Jan 2, priced at $390 found 4 hours ago
Sun, Dec 28 - Tue, Dec 30
IAD
Washington Dulles Intl.
ORD
O'Hare Intl.
$431 Roundtrip, found 4 hours ago
$431
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sun, Dec 28 from Washington Dulles Intl. to O'Hare Intl., returning Tue, Dec 30, priced at $431 found 4 hours ago

Airfares from $29 One Way, $58 Round Trip from Hagerstown to Chicago

Prices starting at $58 for return flights and $29 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, Jan 15 - Sun, Jan 18
BWI
Baltimore
ORD
Chicago
$58 Roundtrip, just found
$58
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Jan 15 from Baltimore to Chicago, returning Sun, Jan 18, priced at $58 just found
Wed, Jan 7 - Wed, Jan 14
BWI
Baltimore
ORD
Chicago
$123 Roundtrip, found 2 days ago
$123
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Jan 7 from Baltimore to Chicago, returning Wed, Jan 14, priced at $123 found 2 days ago
Wed, Jan 21 - Thu, Jan 22
DCA
Washington
ORD
Chicago
$145 Roundtrip, found 5 days ago
$145
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Jan 21 from Washington to Chicago, returning Thu, Jan 22, priced at $145 found 5 days ago
Sat, Feb 21 - Mon, Feb 23
IAD
Washington
MDW
Chicago
$145 Roundtrip, found 1 day ago
$145
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Feb 21 from Washington to Chicago, returning Mon, Feb 23, priced at $145 found 1 day ago
Sat, Feb 7 - Mon, Feb 9
IAD
Washington
ORD
Chicago
$147 Roundtrip, found 2 days ago
$147
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Feb 7 from Washington to Chicago, returning Mon, Feb 9, priced at $147 found 2 days ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (2,229 reviews)

Feb 5 - Feb 9

4 night stay

Baltimore (BWI) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $402, price is now $284 per person
$284
per person
found 1 day ago
Courteous staff, clean room, conveniently located right on the pier.

Reviewed on Nov 3, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,790 reviews)

Feb 12 - Feb 15

3 night stay

Baltimore (BWI) to Chicago (ORD)

Frontier Airlines • Coach

Chicago (ORD) to Baltimore (BWI)

Delta • Coach
Save 100% on your flight
Price was $569, price is now $373 per person
$373
per person
found 1 day ago
Enjoyed our stay in Chicago...coldest weekend ever, but the accommodations were tip-top. Room was clean and well appointed. Staff was incredibly attentive and responsive. The breakfast buffet was very good and a great value for this well located hotel.

Reviewed on Dec 15, 2025

Swissotel - Chicago
4.5-star property

Swissotel - Chicago

9/10 Wonderful! (2,947 reviews)

Feb 12 - Feb 15

3 night stay

Baltimore (BWI) to Chicago (ORD)

Frontier Airlines • Coach

Chicago (ORD) to Baltimore (BWI)

Delta • Coach
Save 100% on your flight
Price was $509, price is now $347 per person
$347
per person
found 1 day ago
Staff was friendly. Rooms are showing their age. No pool, no sauna, nothing really fancy. Not worth the price.

Reviewed on Dec 10, 2025

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Chicago first class flight packages

Price found within the past 48 hours. Click for updated prices.
The Drake Oak Brook, Autograph Collection
3.5-star property

The Drake Oak Brook, Autograph Collection

8.8/10 Excellent! (1,002 reviews)

Feb 5 - Feb 8

3 night stay

Baltimore (BWI) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $668, price is now $602 per person
$602
per person
found 2 hours ago
Excellent accommodations, friendly staff for a weekend getaway.

Reviewed on Jul 25, 2025

Hilton Chicago O'Hare Airport
4.0-star property

Hilton Chicago O'Hare Airport

8.2/10 Very Good! (2,158 reviews)

Feb 5 - Feb 8

3 night stay

Baltimore (BWI) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $854, price is now $715 per person
$715
per person
found 2 hours ago
Awesome hotel, an island of peace and calm and first class treatment in a sea of chaos at O'Hare airport. Staff, restaurant, services--worth every penny. Early departure? Stay here the night before. We did. Calmly woke up and walked to the terminal thru the underground walkways. Truly pleasant and memorable stay.

Reviewed on Nov 11, 2025

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
4.5-star property

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

9.4/10 Exceptional! (1,001 reviews)

Feb 5 - Feb 8

3 night stay

Baltimore (BWI) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $798, price is now $730 per person
$730
per person
found 2 hours ago
Phenomenal location, so many things within walking distance

Reviewed on May 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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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.

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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.