$50 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 - Thu, Oct 2
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$156 Roundtrip, found 7 hours ago
$156
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Sun, Sep 28 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Thu, Oct 2, priced at $156 found 7 hours ago
Sun, Sep 28 - Thu, Oct 2
IAD
Washington Dulles Intl.
MDW
Midway Intl.
$156 Roundtrip, found 10 hours ago
$156
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Sun, Sep 28 from Washington Dulles Intl. to Midway Intl., returning Thu, Oct 2, priced at $156 found 10 hours ago
Sat, Sep 27 - Mon, Sep 29
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$179 Roundtrip, just found
$179
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Sep 27 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Mon, Sep 29, priced at $179 just found
Sat, Sep 27 - Wed, Oct 1
DCA
Ronald Reagan Washington National
ORD
O'Hare Intl.
$263 Roundtrip, found 8 hours ago
$263
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sat, Sep 27 from Ronald Reagan Washington National to O'Hare Intl., returning Wed, Oct 1, priced at $263 found 8 hours ago

Airfares from $50 One Way, $100 Round Trip from Hagerstown to Chicago

Prices starting at $100 for return flights and $50 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, Dec 4 - Thu, Dec 11
BWI
Baltimore
ORD
Chicago
$100 Roundtrip, found 6 hours ago
$100
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Thu, Dec 4 from Baltimore to Chicago, returning Thu, Dec 11, priced at $100 found 6 hours ago
Fri, Oct 24 - Fri, Nov 7
BWI
Baltimore
ORD
Chicago
$100 Roundtrip, found 6 hours ago
$100
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Fri, Oct 24 from Baltimore to Chicago, returning Fri, Nov 7, priced at $100 found 6 hours ago
Sat, Oct 18 - Mon, Oct 20
BWI
Baltimore
MDW
Chicago
$105 Roundtrip, found 5 days ago
$105
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Oct 18 from Baltimore to Chicago, returning Mon, Oct 20, priced at $105 found 5 days ago
Sat, Nov 1 - Tue, Nov 4
BWI
Baltimore
RFD
Rockford
$140 Roundtrip, found 4 days ago
$140
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Nov 1 from Baltimore to Rockford, returning Tue, Nov 4, priced at $140 found 4 days ago
Sat, Oct 25 - Tue, Oct 28
BWI
Baltimore
ORD
Chicago
$141 Roundtrip, found 10 hours ago
$141
Roundtrip
found 10 hours ago
Select Southwest Airlines flight, departing Sat, Oct 25 from Baltimore to Chicago, returning Tue, Oct 28, priced at $141 found 10 hours ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,427 reviews)

Oct 24 - Oct 26

2 night stay

Baltimore (BWI) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $970, price is now $584 per person
$584
per person
found 1 day ago
One day didn’t receive room service

Reviewed on Sep 2, 2025

Park Hyatt Chicago
5.0-star property

Park Hyatt Chicago

9.6/10 Exceptional! (1,001 reviews)

Nov 14 - Nov 17

3 night stay

Baltimore (BWI) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,241, price is now $863 per person
$863
per person
found 1 day ago
From the moment you walk into their lobby at the hotel, you enter a place of calm and relaxation. We stayed in a room with the Water Tower view, and if you have that as the option, take it. It was a beautiful sight to see waking up every morning. This hotel like their other properties are in a class of their own.

Reviewed on Sep 13, 2024

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,716 reviews)

Oct 24 - Oct 26

2 night stay

Baltimore (BWI) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $921, price is now $658 per person
$658
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

If you are looking to find the best deals on Hagerstown to Chicago flights, look no further than Orbitz. Orbitz offers guaranteed low prices as well as cutting-edge mobile tools to help you book cheap flights from Hagerstown to Chicago.

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Orbitz looks for the best deals on Hagerstown to Chicago flights for you. Mix and match airlines for your departing and return flights to fit your travel schedule and budget.

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.