$42 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, Aug 3 - Wed, Aug 6
IAD
Washington Dulles Intl.
MDW
Midway Intl.
$201 Roundtrip, found 10 hours ago
$201
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Sun, Aug 3 from Washington Dulles Intl. to Midway Intl., returning Wed, Aug 6, priced at $201 found 10 hours ago
Sun, Aug 3 - Sun, Sep 7
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$202 Roundtrip, found 4 hours ago
$202
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Sun, Aug 3 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Sun, Sep 7, priced at $202 found 4 hours ago
Sun, Aug 3 - Wed, Aug 6
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$217 Roundtrip, found 10 hours ago
$217
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Sun, Aug 3 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Wed, Aug 6, priced at $217 found 10 hours ago
Sun, Aug 3 - Tue, Aug 5
IAD
Washington Dulles Intl.
ORD
O'Hare Intl.
$221 Roundtrip, found 5 hours ago
$221
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sun, Aug 3 from Washington Dulles Intl. to O'Hare Intl., returning Tue, Aug 5, priced at $221 found 5 hours ago

Airfares from $42 One Way, $70 Round Trip from Hagerstown to Chicago

Prices starting at $70 for return flights and $42 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 - Thu, Oct 23
BWI
Baltimore
MDW
Chicago
$70 Roundtrip, found 2 days ago
$70
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Oct 20 from Baltimore to Chicago, returning Thu, Oct 23, priced at $70 found 2 days ago
Mon, Sep 29 - Sun, Oct 19
BWI
Baltimore
ORD
Chicago
$75 Roundtrip, found 2 days ago
$75
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Sep 29 from Baltimore to Chicago, returning Sun, Oct 19, priced at $75 found 2 days ago
Fri, Oct 31 - Sun, Nov 2
BWI
Baltimore
ORD
Chicago
$91 Roundtrip, just found
$91
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Oct 31 from Baltimore to Chicago, returning Sun, Nov 2, priced at $91 just found
Wed, Sep 24 - Sat, Sep 27
IAD
Washington
ORD
Chicago
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Select United flight, departing Wed, Sep 24 from Washington to Chicago, returning Sat, Sep 27, priced at $157 found 2 days ago
Wed, Sep 24 - Sat, Sep 27
DCA
Washington
ORD
Chicago
$160 Roundtrip, found 2 days ago
$160
Roundtrip
found 2 days ago
Select United flight, departing Wed, Sep 24 from Washington to Chicago, returning Sat, Sep 27, priced at $160 found 2 days ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Staybridge Suites, Lincolnshire by IHG
3.0-star property

Staybridge Suites, Lincolnshire by IHG

8.8/10 Excellent! (1,001 reviews)

Sep 18 - Sep 23

5 night stay

Baltimore (BWI) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
per person
found 12 hours ago
Liked the convenience of the kitchenette and indoor pool. Didn't like the outdated, extremely loud AC system; it sounds like an aircraft when turned on. And on the weekends, there are drunk folks next door who scream and sing after 11 pm. One of the staff should periodically walk the floors after 11 pm to assess what is happening in the rooms.

Reviewed on Jun 29, 2025

Hampton Inn Crown Point
2.5-star property

Hampton Inn Crown Point

9.4/10 Exceptional! (509 reviews)

Sep 18 - Sep 23

5 night stay

Baltimore (BWI) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 12 hours ago
Location is central to family in Hebron, mall at Merrillville, and the highway. Used the full service car wash across the street. Nice breakfast bar. Very friendly staff. Beds were very comfortable.

Reviewed on Mar 1, 2025

Park Hyatt Chicago
5.0-star property

Park Hyatt Chicago

9.6/10 Exceptional! (1,000 reviews)

Aug 29 - Sep 1

3 night stay

Baltimore (BWI) to Chicago (ORD)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
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

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Chicago packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
4.0-star property

The Allegro Royal Sonesta Hotel Chicago Loop

8.8/10 Excellent! (1,837 reviews)

Sep 15 - Sep 21

6 night stay

Baltimore (BWI) to Chicago (ORD)

Delta • Non-stop • PremiumEconomy

Chicago (ORD) to Baltimore (BWI)

United • Non-stop • PremiumEconomy
Save 100% on your flight
per person
found 1 day ago
Attitude of the people was outstanding!! Very friendly and helpful.

Reviewed on Jun 13, 2025

Park Hyatt Chicago
5.0-star property

Park Hyatt Chicago

9.6/10 Exceptional! (1,000 reviews)

Sep 15 - Sep 21

6 night stay

Baltimore (BWI) to Chicago (ORD)

Delta • Non-stop • PremiumEconomy

Chicago (ORD) to Baltimore (BWI)

United • Non-stop • PremiumEconomy
Save 100% on your flight
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

LondonHouse Chicago, Curio Collection by Hilton
4.5-star property

LondonHouse Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (3,357 reviews)

Sep 15 - Sep 21

6 night stay

Baltimore (BWI) to Chicago (ORD)

Delta • Non-stop • PremiumEconomy

Chicago (ORD) to Baltimore (BWI)

United • Non-stop • PremiumEconomy
Save 100% on your flight
per person
found 1 day ago
Unbelievable property, great hospitality, clean, beautiful rooms, lots of amenities, and of course there is the rooftop. I like that they allow guests to have priority on the rooftop in terms of going up there. We will be back for sure. Thank you, London house.!

Reviewed on Jun 15, 2025

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See all available trips from Hagerstown to Chicago
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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.

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.