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$63+ 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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — CHI
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
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 December 4, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/2. 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.
Wed 12/108:00 amBWI - ORD
1 stop7h 31mFrontier
Sun 12/145:11 amORD - BWI
Nonstop2h 07mFrontier
Deal found 12/2$106
This Frontier deal was found by Cheapflights users on 12/3. 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.
Sun 12/2110:00 pmPHL - ORD
1 stop11h 47mFrontier
Sun 1/113:32 pmORD - PHL
Nonstop2h 15mFrontier
Deal found 12/3$111
This deal was found by Cheapflights users on 12/3. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/153:36 pmBWI - ORD
Nonstop2h 18mFrontier
Mon 1/51:44 pmORD - BWI
Nonstop2h 07mFrontier
Deal found 12/3$111
This United Airlines deal was found by Cheapflights users on 12/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:27 amPHL - ORD
Nonstop2h 28mUnited Airlines
Wed 1/78:56 amORD - PHL
Nonstop2h 11mUnited Airlines
Deal found 12/2$115
This Kiwi.com deal was found by Cheapflights users on 12/4. 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 12/1612:20 pmPHL - ORD
1 stop7h 26mFrontier
Wed 12/178:00 amORD - PHL
1 stop7h 52mFrontier
Deal found 12/4$117
This Kiwi.com deal was found by Cheapflights users on 12/3. 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.
Wed 12/173:45 pmPHL - ORD
1 stop24h 17mFrontier
Fri 1/99:34 amORD - PHL
Nonstop2h 15mFrontier
Deal found 12/3$118
This Kiwi.com deal was found by Cheapflights users on 12/2. 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.
Mon 12/153:36 pmBWI - ORD
Nonstop2h 18mFrontier
Tue 12/164:22 pmORD - BWI
1 stop7h 02mFrontier
Deal found 12/2$118
This Kiwi.com deal was found by Cheapflights users on 12/3. 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.
Wed 12/1012:20 pmPHL - ORD
1 stop7h 26mFrontier
Wed 12/178:00 amORD - PHL
1 stop7h 52mFrontier
Deal found 12/3$120
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 12/98:00 amBWI - ORD
1 stop8h 12mFrontier
Tue 12/164:22 pmORD - BWI
1 stop7h 02mFrontier
Deal found 12/2$122
This Frontier deal was found by Cheapflights users on 12/3. 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 12/199:40 amPHL - ORD
Nonstop2h 30mFrontier
Sun 1/113:32 pmORD - PHL
Nonstop2h 15mFrontier
Deal found 12/3$123
This Frontier deal was found by Cheapflights users on 12/1. 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.
Mon 12/153:36 pmBWI - ORD
Nonstop2h 18mFrontier
Fri 1/21:40 pmORD - BWI
Nonstop2h 07mFrontier
Deal found 12/1$124
This Priceline deal was found by Cheapflights users on 12/3. 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.
Mon 12/153:36 pmBWI - ORD
Nonstop2h 18mFrontier
Mon 12/156:30 pmORD - BWI
Nonstop2h 07mFrontier
Deal found 12/3$125

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 December 4, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$96
(Kiwi.com)

One-way from

$63
(Southwest)

Popular in

November

Cheapest in

September

Average price

$264

Good round-trip deal

$167 or less

Good one-way deal

$97 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. 5% potential increase in price ($14 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 December 2025
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 December 4, 2025.
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

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Thu 1/8

5:00 pm-6:30 pm

Nonstop2h 30m

Chicago O'Hare Intl

Mon 1/12

8:56 am-12:07 pm

Nonstop2h 11m

$105

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 1/8

7:45 am-9:05 am

Nonstop2h 20m

Chicago Midway

Mon 1/12

5:15 pm-8:10 pm

Nonstop1h 55m

$105

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Mon 1/12

1:45 pm-2:55 pm

Nonstop2h 10m

Chicago Midway

Mon 1/12

5:15 pm-8:10 pm

Nonstop1h 55m

$105

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Thu 2/5

10:05 am-11:25 am

Nonstop2h 20m

Chicago O'Hare Intl

Sat 2/7

6:15 pm-9:21 pm

Nonstop2h 06m

$105

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Sat 2/21

6:20 am-7:43 am

Nonstop2h 23m

Chicago O'Hare Intl

Sat 2/28

6:25 pm-9:27 pm

Nonstop2h 02m

$105

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Mon 1/12

10:05 am-11:25 am

Nonstop2h 20m

Chicago O'Hare Intl

Mon 1/12

6:15 pm-9:21 pm

Nonstop2h 06m

$105

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Fri 1/9

5:00 pm-6:30 pm

Nonstop2h 30m

Chicago O'Hare Intl

Tue 1/13

11:20 am-2:31 pm

Nonstop2h 11m

$109

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Wed 1/21

10:10 am-11:38 am

Nonstop2h 28m

Chicago O'Hare Intl

Fri 1/23

11:20 am-2:31 pm

Nonstop2h 11m

$109

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Fri 1/9

1:45 pm-2:55 pm

Nonstop2h 10m

Chicago Midway

Mon 1/12

5:15 pm-8:10 pm

Nonstop1h 55m

$116

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Fri 2/27

6:30 am-7:53 am

Nonstop2h 23m

Chicago O'Hare Intl

Mon 3/2

6:25 pm-9:27 pm

Nonstop2h 02m

$116

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/4

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 $50). Flying from Maryland to Chicago in June is currently the most expensive (average of $132). 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 December 4, 2025.

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 59% versus a flight at noon.

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 November 29, 2025.

Travelers seeking maximum savings on their Maryland to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Tuesday at noon 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 December 4, 2025.

The most flights from USMD to CHI are scheduled on a Thursday (24 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (8 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 20m. Fly via United Airlines, Southwest, 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 $73 on Frontier and Southwest, respectively.

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

    Most travelers choose Washington, D.C. Reagan-National - Chicago O'Hare Intl, Washington, D.C. Dulles Intl - Chicago O'Hare Intl or Baltimore/Washington - 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 Sun Country Air (100%), Spirit Airlines (100%) or Republic Airways (100%) 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 $653, our data indicates the cheapest price to be $48. The most popular route (Washington, D.C. Reagan-National - Chicago O'Hare Intl), is priced around $105.

  • 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 $50). Flying from Maryland to Chicago in June is currently the most expensive (average of $132). 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 6 airlines flying from Maryland to Chicago

Discover the top 6 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 December 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$52Average$120FlexibilityNo cancel feeOn-time65%
FrontierCheapest$64Average$164FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$328FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$150Average$291FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$158Average$309FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$168Average$317FlexibilityNo cancel feeOn-time71%

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