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$58+ Cheap flights from Maryland to Chicago (CHI)

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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — CHI
פב​​​​​​​' 22 — מרץ 11
א' 2/22
א' 3/1
1 adult, Economy
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Cheap flight deals from Maryland to Chicago

Cheapest flights from Maryland to Chicago
Explore the most affordable flight options available from Maryland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on ינואר 23, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/22. 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.
א' 2/19:20 am
BWI
-
ORD
Nonstop2h 27m
Frontier
ב' 2/28:45 am
ORD
-
BWI
Nonstop2h 00m
Frontier
Deal found 1/22$86
This Frontier deal was found by Cheapflights users on 1/22. 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.
ה' 3/59:19 am
BWI
-
ORD
Nonstop2h 27m
Frontier
ו' 4/36:15 am
ORD
-
BWI
Nonstop2h 06m
Frontier
Deal found 1/22$87
This Expedia deal was found by Cheapflights users on 1/22. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ג' 2/2412:30 pm
BWI
-
ORD
1 stop7h 41m
Multiple Airlines
ה' 2/265:15 am
ORD
-
BWI
Nonstop2h 09m
Multiple Airlines
Deal found 1/22$91
This Priceline deal was found by Cheapflights users on 1/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ו' 1/3010:00 am
BWI
-
ORD
Nonstop2h 27m
Multiple Airlines
ו' 2/68:43 pm
ORD
-
BWI
1 stop10h 48m
Multiple Airlines
Deal found 1/20$92
This Frontier deal was found by Cheapflights users on 1/21. 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.
ב' 2/912:40 pm
BWI
-
ORD
Nonstop2h 27m
Frontier
ד' 2/1112:36 pm
ORD
-
BWI
1 stop10h 55m
Frontier
Deal found 1/21$93
This Frontier deal was found by Cheapflights users on 1/22. 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.
ה' 3/59:19 am
BWI
-
ORD
Nonstop2h 27m
Frontier
ה' 4/21:19 pm
ORD
-
BWI
Nonstop2h 05m
Frontier
Deal found 1/22$95
This Priceline deal was found by Cheapflights users on 1/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ה' 3/59:19 am
BWI
-
ORD
Nonstop2h 27m
Frontier
ו' 3/612:43 pm
ORD
-
BWI
Nonstop2h 00m
Frontier
Deal found 1/20$97
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
ה' 2/197:19 pm
BWI
-
ORD
Nonstop2h 27m
Frontier
ה' 2/264:42 pm
ORD
-
BWI
1 stop6h 49m
Frontier
Deal found 1/20$98
This Frontier deal was found by Cheapflights users on 1/22. 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.
א' 3/19:59 pm
BWI
-
ORD
Nonstop2h 27m
Frontier
ו' 4/36:15 am
ORD
-
BWI
Nonstop2h 06m
Frontier
Deal found 1/22$99
This Frontier deal was found by Cheapflights users on 1/22. 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.
ה' 3/59:19 am
BWI
-
ORD
Nonstop2h 27m
Frontier
ב' 3/3012:45 pm
ORD
-
BWI
Nonstop2h 09m
Frontier
Deal found 1/22$101
This Frontier deal was found by Cheapflights users on 1/22. 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.
ה' 2/195:45 am
BWI
-
ORD
1 stop8h 09m
Frontier
ה' 2/193:15 pm
ORD
-
BWI
Nonstop2h 09m
Frontier
Deal found 1/22$103
This Expedia deal was found by Cheapflights users on 1/22. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ד' 2/187:59 pm
PHL
-
ORD
1 stop28h 25m
Frontier
ג' 2/248:30 am
ORD
-
PHL
1 stop26h 52m
Frontier
Deal found 1/22$128

Find flight deals from Maryland to Chicago

Keep the following information in mind while searching for Maryland to Chicago flight deals. Data was last updated ינואר 23, 2026.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$86
(Kiwi.com)

One-way from

$58
(Super.com)

Popular in

December

Cheapest in

September

Average price

$247

Good round-trip deal

$167 or less

Good one-way deal

$125 or less
Provider with most accurate pricing for Washington, D.C. (WAS)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Washington, D.C. (WAS)-Chicago (CHI) flights.
Search Deals
From Maryland to Chicago (CHI)
Search Deals
One-way flight from Maryland to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Maryland to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Maryland to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Maryland to Chicago 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 ינואר 23, 2026.
Use the filters below to find and compare flights from Maryland to Chicago that are best for you.

Fly from

Maryland

Fly to

Chicago

Route

Depart

Return

Price

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

ה' 3/5

9:19 am-10:46 am

Nonstop2h 27m

Chicago O'Hare Intl

ב' 3/9

7:11 pm-10:53 pm

2 stops26h 42m

$126

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

ו' 2/27

12:40 pm-1:50 pm

Nonstop2h 10m

Chicago Midway

ב' 3/2

7:05 pm-9:55 pm

Nonstop1h 50m

$158

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

ה' 2/12

6:30 am-7:53 am

Nonstop2h 23m

Chicago O'Hare Intl

ש' 2/14

6:15 pm-9:17 pm

Nonstop2h 02m

$159

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

ש' 2/21

10:29 am-9:33 pm

1 stop12h 04m

Chicago Midway

ב' 2/23

6:00 am-4:08 pm

1 stop9h 08m

$160

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

ה' 4/9

5:34 pm-10:21 pm

1 stop5h 47m

Chicago Midway

ש' 4/11

2:56 pm-12:41 am

1 stop8h 45m

$160

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

ש' 4/11

5:16 pm-10:29 pm

1 stop6h 13m

Chicago Midway

ד' 4/15

2:20 pm-12:36 am

1 stop9h 16m

$175

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

ג' 2/24

6:00 am-9:54 am

1 stop4h 54m

Chicago Midway

ב' 3/2

6:20 pm-10:53 pm

1 stop3h 33m

$177

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

ו' 2/20

9:35 pm-10:45 pm

Nonstop2h 10m

Chicago Midway

א' 2/22

7:25 am-10:20 am

Nonstop1h 55m

$177

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

ו' 2/13

12:40 pm-1:50 pm

Nonstop2h 10m

Chicago Midway

ש' 2/21

6:15 pm-9:05 pm

Nonstop1h 50m

$179

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

ד' 2/4

7:10 am-6:27 pm

1 stop12h 17m

Chicago O'Hare Intl

ש' 2/7

9:25 am-10:41 pm

1 stop12h 16m

$181

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

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

Have a flexible travel schedule? Discover the best time to fly to Chicago from Maryland 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 Maryland to Chicago

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

Currently, March is the cheapest month in which you can book a flight from Maryland to Chicago (average of $53). Flying from Maryland to Chicago in June is currently the most expensive (average of $133). 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 MD to CHI?

Find hourly flight availability from Maryland to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated ינואר 23, 2026.

When flying from Maryland to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 45% versus a flight in the morning.

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

Use this chart to determine the cheapest time to fly round-trip from Maryland to Chicago. Price data was last updated on January 17, 2026.

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

Weekly flight availability from Maryland to Chicago

Explore weekly flight availability from Maryland to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated ינואר 23, 2026.

The most flights from USMD to CHI are scheduled on a Friday (19 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 on average).

Related info for your journey

Find useful and relevant information for your journey from Maryland to Chicago. 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 Maryland to Chicago?

    There are many flights that can get you from Maryland to Chicago in 2h 10m. Fly via Southwest, United Airlines, or Frontier to get the fastest option. The distance between Maryland and Chicago is about 609 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $42. Users have also found prices from $44 and $69 on Frontier and American Airlines, respectively.

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

    Most travelers choose Washington, D.C. Reagan-National - Chicago O'Hare Intl, Baltimore/Washington - Chicago O'Hare Intl or Washington, D.C. Dulles Intl - Chicago O'Hare Intl when deciding on the best route from Maryland to Chicago.

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

    No one likes to see their flight delayed. When booking a flight from Maryland to Chicago consider choosing Cathay Pacific (85%), Republic Airways (84%) or Royal Jordanian (82%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Maryland to Chicago?

    Looking for the cheapest flight from Maryland to Chicago? While on average our users pay $625, our data indicates the cheapest price to be $32. The most popular route (Washington, D.C. Reagan-National - Chicago O'Hare Intl), is priced around $184.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Maryland to Chicago 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 Maryland to Chicago?

    Currently, March is the cheapest month in which you can book a flight from Maryland to Chicago (average of $53). Flying from Maryland to Chicago in June is currently the most expensive (average of $133). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Maryland to Chicago

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

Discover the top 5 airlines that operate flights from Maryland to Chicago. 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 ינואר 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$41Average$115FlexibilityNo cancel feeOn-time65%
FrontierCheapest$57Average$160FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$148Average$292FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$153Average$304FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$159Average$316FlexibilityNo cancel feeOn-time71%

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