$44 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.

Sun, Sep 28 - Wed, Oct 1
IAD
Washington Dulles Intl.
MDW
Midway Intl.
$156 Roundtrip, found 3 hours ago
$156
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sun, Sep 28 from Washington Dulles Intl. to Midway Intl., returning Wed, Oct 1, priced at $156 found 3 hours ago
Sun, Sep 28 - Wed, Oct 1
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$156 Roundtrip, found 3 hours ago
$156
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sun, Sep 28 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Wed, Oct 1, priced at $156 found 3 hours ago
Sun, Sep 28 - Sat, Oct 4
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$167 Roundtrip, found 1 hour ago
$167
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sun, Sep 28 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Sat, Oct 4, priced at $167 found 1 hour ago
Sun, Sep 28 - Wed, Oct 1
IAD
Washington Dulles Intl.
ORD
O'Hare Intl.
$295 Roundtrip, found 3 hours ago
$295
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sun, Sep 28 from Washington Dulles Intl. to O'Hare Intl., returning Wed, Oct 1, priced at $295 found 3 hours ago

Airfares from $44 One Way, $99 Round Trip from Hagerstown to Chicago

Prices starting at $99 for return flights and $44 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.

Mon, Oct 20 - Mon, Oct 27
BWI
Baltimore
ORD
Chicago
$99 Roundtrip, found 11 hours ago
$99
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Mon, Oct 20 from Baltimore to Chicago, returning Mon, Oct 27, priced at $99 found 11 hours ago
Thu, Dec 11 - Sun, Dec 14
BWI
Baltimore
ORD
Chicago
$100 Roundtrip, found 4 hours ago
$100
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Thu, Dec 11 from Baltimore to Chicago, returning Sun, Dec 14, priced at $100 found 4 hours ago
Sat, Oct 18 - Mon, Oct 20
BWI
Baltimore
MDW
Chicago
$105 Roundtrip, found 4 days ago
$105
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Oct 18 from Baltimore to Chicago, returning Mon, Oct 20, priced at $105 found 4 days ago
Sat, Nov 1 - Tue, Nov 4
BWI
Baltimore
RFD
Rockford
$140 Roundtrip, found 3 days ago
$140
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Nov 1 from Baltimore to Rockford, returning Tue, Nov 4, priced at $140 found 3 days ago
Sat, Nov 1 - Tue, Nov 4
BWI
Baltimore
MDW
Chicago
$141 Roundtrip, found 9 hours ago
$141
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Sat, Nov 1 from Baltimore to Chicago, returning Tue, Nov 4, priced at $141 found 9 hours ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
4.5-star property

Fairmont Chicago at Millennium Park

8.6/10 Excellent! (1,920 reviews)

Nov 14 - Nov 17

3 night stay

Baltimore (BWI) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $625, price is now $459 per person
$459
per person
found 1 day ago
The only restaurant was over priced, waiter was not pleasant, although there were few people there. When we left the room for the day, cleaning women ask if we needed anything, as to say she didn’t plan on doing anything to our room. We did ask for clean towels, and she brought them. For what we paid for this room, we expected much more

Reviewed on Aug 22, 2025

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! (2,142 reviews)

Nov 14 - Nov 17

3 night stay

Baltimore (BWI) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $853, price is now $606 per person
$606
per person
found 1 day ago
nothing bad to say about this property. Had a water view on the top floor and it was amazing! would definitely go back

Reviewed on Sep 16, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,716 reviews)

Nov 7 - Nov 9

2 night stay

Baltimore (BWI) to Chicago (ORD)

Spirit Airlines • Coach

Chicago (ORD) to Baltimore (BWI)

Frontier Airlines • Coach
Price was $811, price is now $582 per person
$582
per person
found 1 day ago
Every employee makes every guest feel like a rockstar. Commitment to quality and guest experience is evident.

Reviewed on Sep 14, 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
610 mi
Direct Flight Airlines
American Airlines, Qatar Airways, JAL, Alaska Airlines, Cathay Pacific, Emirates, Royal Jordanian, ANA, Air New Zealand, United Airlines, British Airways
Earliest Flight Arrival
11:39AM UTC
Latest Flight Arrival
3:48AM UTC

Hagerstown to Chicago

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You can get email, SMS text, or voicemail updates regarding any major changes to your flights from Hagerstown to Chicago. These free alerts can also be sent to as many as six additional contacts, ensuring that your friends, colleagues, or family are aware of changes to your arrival time.

Stay in Your Budget and Still Get Great Accommodations

Orbitz shoppers can access affordable vacation packages and have the option of booking their departure and arrival flights through different airlines, making travel less costly and more convenient. The best prices on flights from Hagerstown to Chicagoare always found on Orbitz.

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.