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$55+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — CHI
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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Cheap flight deals from Maryland to Chicago

Keep the following information in mind while searching for Maryland to Chicago flight deals. Data was last updated November 6, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$106
(Kiwi.com)

One-way from

$55
(Priceline)

Popular in

April

Cheapest in

September

Average price

$264

Good round-trip deal

$167 or less

Good one-way deal

$103 or less
Provider with most accurate pricing for Washington, D.C. (WAS)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Washington, D.C. (WAS)-Chicago (CHI) flights.
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From Maryland to Chicago (CHI)
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One-way flight from Maryland to Chicago (CHI)
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Highest demand for flights based on searches. 7% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip flight from Maryland to Chicago (CHI).
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Price to beat on a one-way flight from Maryland to Chicago (CHI).
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Find 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 November 6, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/176:00 amPHL - ORD
Nonstop2h 26mFrontier
Mon 11/1711:53 amORD - PHL
1 stop11h 46mFrontier
Deal found 11/5$106
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 11/244:50 pmPHL - MDW
Nonstop2h 16mFrontier
Thu 11/274:00 pmMDW - PHL
1 stop22h 56mFrontier
Deal found 11/6$106
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/176:00 amPHL - ORD
Nonstop2h 26mFrontier
Tue 11/1812:37 pmORD - PHL
1 stop19h 35mFrontier
Deal found 11/5$107
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Thu 11/206:09 pmPHL - MDW
Nonstop2h 22mMultiple Airlines
Thu 11/276:05 amMDW - PHL
1 stop10h 27mMultiple Airlines
Deal found 11/5$107
This Frontier deal was found by Cheapflights users on 11/6. 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.
Thu 12/46:00 amPHL - ORD
1 stop8h 08mFrontier
Fri 12/52:00 pmORD - PHL
Nonstop2h 15mFrontier
Deal found 11/6$109
This Priceline deal was found by Cheapflights users on 11/6. 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.
Thu 12/46:00 amPHL - ORD
1 stop8h 08mFrontier
Sat 12/61:24 pmORD - PHL
1 stop10h 17mFrontier
Deal found 11/6$110
This Priceline deal was found by Cheapflights users on 11/6. 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.
Thu 12/1111:07 amPHL - MDW
1 stop11h 46mFrontier
Mon 12/1512:35 pmMDW - PHL
1 stop10h 59mFrontier
Deal found 11/6$110
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/249:37 amPHL - ORD
Nonstop2h 34mMultiple Airlines
Tue 12/24:22 pmORD - PHL
1 stop7h 04mMultiple Airlines
Deal found 11/5$111
This Priceline deal was found by Cheapflights users on 11/5. 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.
Sat 12/64:00 pmPHL - ORD
1 stop9h 09mMultiple Airlines
Tue 12/910:00 amORD - PHL
1 stop5h 31mMultiple Airlines
Deal found 11/5$112
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 11/244:50 pmPHL - MDW
Nonstop2h 16mMultiple Airlines
Tue 12/22:49 pmMDW - PHL
1 stop8h 37mMultiple Airlines
Deal found 11/6$113
This Super.com deal was found by Cheapflights users on 11/5. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/155:50 amPHL - ORD
1 stop6h 40mFrontier
Mon 11/178:26 amORD - PHL
Nonstop2h 13mFrontier
Deal found 11/5$117
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/196:50 pmPHL - MDW
1 stop22h 40mFrontier
Fri 11/288:41 pmMDW - PHL
Nonstop1h 57mFrontier
Deal found 11/5$117

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 November 6, 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

Wed 12/10

12:20 pm-6:46 pm

1 stop7h 26m

Chicago O'Hare Intl

Fri 12/12

3:14 pm-11:15 pm

1 stop7h 01m

$123

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Wed 1/14

6:30 am-7:59 am

Nonstop2h 29m

Chicago O'Hare Intl

Sat 1/17

2:30 pm-5:34 pm

Nonstop2h 04m

$139

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Sat 2/21

5:30 am-6:55 am

Nonstop2h 25m

Chicago Midway

Sat 2/28

10:15 am-1:10 pm

Nonstop1h 55m

$139

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Mon 1/12

10:25 am-11:35 am

Nonstop2h 10m

Chicago Midway

Thu 1/15

10:45 am-1:35 pm

Nonstop1h 50m

$139

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Fri 11/21

6:00 am-5:39 pm

1 stop12h 39m

Chicago O'Hare Intl

Sun 11/23

12:29 pm-8:59 am

1 stop19h 30m

$144

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Fri 11/21

9:18 am-5:39 pm

1 stop9h 21m

Chicago O'Hare Intl

Mon 11/24

6:30 am-10:19 am

1 stop26h 49m

$144

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 12/6

5:45 am-11:54 am

1 stop7h 09m

Chicago O'Hare Intl

Sat 12/13

1:24 pm-11:05 pm

1 stop8h 41m

$146

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 1/7

12:15 pm-1:30 pm

Nonstop2h 15m

Chicago Midway

Mon 1/12

10:00 am-12:55 pm

Nonstop1h 55m

$148

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 2/13

5:15 am-6:30 am

Nonstop2h 15m

Chicago Midway

Sun 2/15

9:40 am-12:35 pm

Nonstop1h 55m

$148

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sun 2/1

8:15 pm-9:25 pm

Nonstop2h 10m

Chicago Midway

Tue 2/3

5:15 pm-8:10 pm

Nonstop1h 55m

$148

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

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 November 6, 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 61% 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 2, 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 November 6, 2025.

The most flights from USMD to CHI are scheduled on a Thursday (26 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 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 25m. Fly via Frontier, United Airlines, or Southwest to get the fastest option. The distance between Maryland and Chicago is about 666 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 Frontier. According to our data, you can fly for as low as $68. Users have also found prices from $70 and $70 on United Airlines and Southwest, respectively.

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

    Most travelers choose Washington, D.C. Dulles Intl - Chicago O'Hare Intl, Baltimore/Washington - Chicago O'Hare Intl or Washington, D.C. Reagan-National - 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 ANA (93%) 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 $909, our data indicates the cheapest price to be $56. The most popular route (Washington, D.C. Dulles Intl - Chicago O'Hare Intl), is priced around $143.

  • 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
Hammond
Porter
Benton Harbor
Merrillville

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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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$52Average$120FlexibilityNo cancel feeOn-time65%
FrontierCheapest$69Average$167FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$328FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$156Average$294FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$158Average$308FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$166Average$313FlexibilityNo cancel feeOn-time71%

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