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$54+ Cheap flights from Chicago (CHI) to Maryland

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BWI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap flight deals from Chicago to Maryland

Keep the following information in mind while searching for Chicago to Maryland flight deals. Data was last updated October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$95
(Kiwi.com)

One-way from

$54
(Kiwi.com)

Popular in

January

Cheapest in

August

Average price

$257

Good round-trip deal

$140 or less

Good one-way deal

$87 or less
Provider with most accurate pricing for Chicago (CHI)-Washington, D.C. (WAS) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Washington, D.C. (WAS) flights.
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From Chicago (CHI) to Maryland
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One-way flight from Chicago (CHI) to Maryland
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Highest demand for flights based on searches. 5% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Maryland.
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Price to beat on a one-way flight from Chicago (CHI) to Maryland.
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Find flight deals from Chicago to Maryland

Cheapest flights from Chicago to Maryland
Explore the most affordable flight options available from Chicago to Maryland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/258:35 amORD - BWI
Nonstop1h 59mFrontier
Sun 2/228:58 amBWI - ORD
Nonstop2h 24mFrontier
Deal found 10/29$95
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2212:25 pmMDW - BWI
Nonstop1h 56mFrontier
Mon 11/244:06 pmBWI - MDW
Nonstop2h 09mFrontier
Deal found 10/30$96
This CheapOair deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/151:37 pmMDW - BWI
1 stop9h 25mFrontier
Mon 11/177:25 pmBWI - MDW
Nonstop2h 06mFrontier
Deal found 10/28$97
This CheapOair deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/155:45 pmORD - BWI
1 stop5h 17mFrontier
Mon 11/174:02 pmBWI - ORD
Nonstop2h 16mFrontier
Deal found 10/28$97
This CheapOair deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/174:01 pmORD - BWI
1 stop7h 23mFrontier
Mon 1/128:58 amBWI - ORD
Nonstop2h 24mFrontier
Deal found 10/28$98
This CheapOair deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/124:20 pmORD - BWI
1 stop7h 12mFrontier
Mon 12/153:36 pmBWI - ORD
Nonstop2h 18mFrontier
Deal found 10/30$100
This Frontier deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/54:20 pmORD - BWI
1 stop7h 12mFrontier
Sun 12/79:13 amBWI - ORD
Nonstop2h 18mFrontier
Deal found 10/30$101
This Kiwi.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1412:04 pmORD - BWI
Nonstop2h 03mFrontier
Mon 11/174:02 pmBWI - ORD
Nonstop2h 16mFrontier
Deal found 10/28$102
This Frontier deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/156:15 amMDW - BWI
1 stop8h 20mFrontier
Sun 11/169:21 amBWI - MDW
Nonstop2h 05mFrontier
Deal found 10/29$103
This Mytrip deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/512:09 pmORD - BWI
1 stop11h 14mMultiple Airlines
Sun 12/79:13 amBWI - ORD
Nonstop2h 18mMultiple Airlines
Deal found 10/28$104
This Orbitz deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1212:09 pmORD - BWI
1 stop11h 14mMultiple Airlines
Mon 12/153:36 pmBWI - ORD
Nonstop2h 18mMultiple Airlines
Deal found 10/28$105
This Frontier deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/131:24 pmORD - BWI
1 stop10h 00mFrontier
Mon 12/153:36 pmBWI - ORD
Nonstop2h 18mFrontier
Deal found 10/28$106

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Maryland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 30, 2025.
Use the filters below to find and compare flights from Chicago to Maryland that are best for you.

Fly from

Chicago

Fly to

Maryland

Route

Depart

Return

Price

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Wed 11/12

12:37 pm-6:29 pm

1 stop4h 52m

Baltimore/Washington

Sat 11/15

4:30 pm-11:29 pm

1 stop7h 59m

$109

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Mon 11/17

9:15 am-12:19 pm

Nonstop2h 04m

Philadelphia

Thu 11/20

6:09 pm-7:31 pm

Nonstop2h 22m

$136

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Mon 1/26

9:50 am-12:40 pm

Nonstop1h 50m

Baltimore/Washington

Tue 1/27

5:50 pm-7:00 pm

Nonstop2h 10m

$139

ChicagoBaltimore

ORD - BWI

ORDBWI

Chicago O'Hare Intl

Mon 1/12

11:05 am-2:11 pm

Nonstop2h 06m

Baltimore/Washington

Wed 1/14

10:05 am-11:25 am

Nonstop2h 20m

$139

ChicagoBaltimore

MDW - BWI

MDWBWI

Chicago Midway

Mon 1/12

5:15 pm-8:10 pm

Nonstop1h 55m

Baltimore/Washington

Wed 1/14

10:25 am-11:35 am

Nonstop2h 10m

$139

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Sat 12/6

11:05 am-2:07 pm

Nonstop2h 02m

Philadelphia

Tue 12/9

10:15 am-11:35 am

Nonstop2h 20m

$139

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Sat 1/17

2:30 pm-5:34 pm

Nonstop2h 04m

Philadelphia

Mon 1/19

6:30 am-7:59 am

Nonstop2h 29m

$148

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Sat 11/15

6:45 am-2:35 pm

1 stop6h 50m

Washington, D.C. Reagan-National

Tue 11/18

4:55 pm-8:52 pm

1 stop4h 57m

$153

ChicagoPhiladelphia

MDW - PHL

MDWPHL

Chicago Midway

Tue 12/2

6:05 pm-9:00 pm

Nonstop1h 55m

Philadelphia

Thu 12/4

6:00 am-7:15 am

Nonstop2h 15m

$158

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Fri 12/5

2:30 pm-5:39 pm

Nonstop2h 09m

Philadelphia

Tue 12/9

6:30 am-7:56 am

Nonstop2h 26m

$158

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 60 results
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Best time to book a flight from Chicago to Maryland

Have a flexible travel schedule? Discover the best time to fly to Maryland from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Maryland

What is the cheapest month to book a flight from Chicago to Maryland?

Currently, February is the cheapest month in which you can book a flight from Chicago to Maryland (average of $57). Flying from Chicago to Maryland in April is currently the most expensive (average of $169). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to MD?

Find hourly flight availability from Chicago to Maryland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

It’s typically best to fly out from Chicago to Maryland in the evening. Doing so could potentially save you 43% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly from Chicago to Maryland?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Maryland. Price data was last updated on October 26, 2025.

Travelers seeking maximum savings on their Chicago to Maryland flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Chicago to Maryland?

Reviews of airlines servicing Maryland

Get insights into the airlines that provide service to Maryland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Maryland. Reviews last updated October 30, 2025.
See what other customers who have flown with Southwest, United Airlines, and American Airlines from Chicago to Maryland have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,243 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,116 reviews
Southwest
8.0
Very good
4,243 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,122 reviews
Southwest
8.0
Very good
4,243 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Chicago to Maryland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Maryland?

    A quick flight from Chicago to Maryland can take about 1h 50m. Frontier provides one of the quickest options available for as low as $139. There are 609 mi between Chicago and Maryland. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago to Maryland one-way?

    The cheapest airlines for a one-way flight from Chicago to Maryland are Frontier ($69), Southwest ($70), and United Airlines ($70).

  • What are the most popular routes from Chicago to Maryland?

    The most popular flight routes from Chicago to Maryland are Chicago O'Hare Intl - Washington, D.C. Dulles Intl, Chicago O'Hare Intl - Baltimore/Washington and Chicago O'Hare Intl - Washington, D.C. Reagan-National.

  • What are the most reliable airlines from Chicago to Maryland?

    Consider Spirit Airlines (100%), Envoy Air (86%) or Southwest (85%) when booking your flight. These represent the most reliable airlines when flying from Chicago to Maryland.

  • What are the cheapest flights from Chicago to Maryland?

    While on average a flight from Chicago to Maryland is generally $283, our data shows the cheapest flight currently is $48. When looking at the most popular route, (Chicago O'Hare Intl - Washington, D.C. Dulles Intl), you can expect to pay $130 for that flight.

  • Can I find deals for flights from Chicago to Maryland that include hotel bookings?

    Yes. In addition to deals on Chicago to Maryland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Maryland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Maryland.

  • Can I find deals for business class flights from Chicago to Maryland?

    Yes. Cheapflights offers flight deals from Chicago to Maryland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Maryland?

    Currently, February is the cheapest month in which you can book a flight from Chicago to Maryland (average of $57). Flying from Chicago to Maryland in April is currently the most expensive (average of $169). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Chicago to Maryland

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Chicago to Maryland

Discover the top 5 airlines that operate flights from Chicago to Maryland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$45Average$147FlexibilityNo cancel feeOn-time65%
FrontierCheapest$63Average$155FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$143Average$275FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$143Average$295FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$147Average$378FlexibilityNo cancel feeOn-time71%

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