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$70+ 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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — CHI
Apr 5 — Apr 121
Sun 4/5
Sun 4/12
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 March 6, 2026.

This Super.com deal was found by Cheapflights users on 3/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/74:25 pm
BWI
-
ORD
Nonstop2h 26m
Frontier
Thu 5/1412:25 pm
ORD
-
BWI
Nonstop2h 05m
Frontier
Deal found 3/1$120
This Expedia deal was found by Cheapflights users on 3/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/174:42 pm
BWI
-
ORD
Nonstop2h 26m
Frontier
Sun 4/1912:44 pm
ORD
-
BWI
Nonstop2h 05m
Frontier
Deal found 3/2$121
This Kiwi.com deal was found by Cheapflights users on 3/3. 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.
Tue 4/1412:17 pm
BWI
-
ORD
1 stop5h 43m
Frontier
Thu 4/1612:42 pm
ORD
-
BWI
Nonstop2h 05m
Frontier
Deal found 3/3$123
This Kiwi.com deal was found by Cheapflights users on 3/2. 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.
Sat 5/212:20 pm
BWI
-
MDW
1 stop7h 17m
Frontier
Tue 5/52:20 pm
MDW
-
BWI
1 stop9h 29m
Frontier
Deal found 3/2$124
This Booking.com deal was found by Cheapflights users on 3/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:05 am
BWI
-
ORD
1 stop6h 27m
Frontier
Mon 4/2012:20 pm
ORD
-
BWI
Nonstop2h 05m
Frontier
Deal found 3/4$124
This Kiwi.com deal was found by Cheapflights users on 3/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:00 am
BWI
-
ORD
1 stop12h 00m
Frontier
Wed 4/291:27 pm
ORD
-
BWI
1 stop18h 50m
Frontier
Deal found 3/1$125
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 4/2812:17 pm
BWI
-
MDW
1 stop8h 14m
Frontier
Wed 5/62:20 pm
MDW
-
BWI
1 stop9h 29m
Frontier
Deal found 3/2$126
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 5/49:21 pm
BWI
-
ORD
1 stop24h 56m
Frontier
Wed 5/64:28 pm
ORD
-
BWI
1 stop7h 21m
Frontier
Deal found 3/2$126
This Super.com deal was found by Cheapflights users on 3/5. 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.
Thu 4/164:42 pm
BWI
-
ORD
Nonstop2h 26m
Frontier
Sun 4/1912:44 pm
ORD
-
BWI
Nonstop2h 05m
Frontier
Deal found 3/5$127
This Kiwi.com deal was found by Cheapflights users on 3/4. 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 4/1412:17 pm
BWI
-
MDW
1 stop8h 14m
Frontier
Sat 4/186:00 am
MDW
-
BWI
1 stop9h 58m
Frontier
Deal found 3/4$128
This Kiwi.com deal was found by Cheapflights users on 3/4. 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 4/73:19 pm
BWI
-
ORD
1 stop8h 20m
Frontier
Wed 4/88:00 am
ORD
-
BWI
Nonstop2h 06m
Frontier
Deal found 3/4$129
This Kiwi.com deal was found by Cheapflights users on 3/3. 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.
Tue 4/1412:17 pm
BWI
-
MDW
1 stop8h 14m
Frontier
Tue 4/216:10 am
MDW
-
BWI
1 stop9h 44m
Frontier
Deal found 3/3$131

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 March 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$120
(Super.com)

One-way from

$70
(Trip.com)

Popular in

December

Cheapest in

September

Average price

$279

Good round-trip deal

$254 or less

Good one-way deal

$146 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. 3% potential increase in price ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 6, 2026.
Use the filters below to find and compare flights from Maryland to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Sat 4/18

5:00 pm-6:28 pm

Nonstop2h 28m

Chicago O'Hare Intl

Tue 4/21

9:55 pm-12:59 am

Nonstop2h 04m

$162

PhiladelphiaChicago

PHL - RFD

PHLRFD

Philadelphia

Wed 4/29

1:30 pm-9:47 am

1 stop21h 17m

Chicago Greater Rockford

Mon 5/4

7:09 pm-11:57 pm

1 stop27h 48m

$171

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Fri 5/15

8:35 pm-10:04 pm

Nonstop2h 29m

Chicago O'Hare Intl

Sun 5/17

6:55 am-9:59 am

Nonstop2h 04m

$177

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Fri 4/17

6:17 am-7:45 am

Nonstop2h 28m

Chicago O'Hare Intl

Wed 4/22

9:55 pm-12:59 am

Nonstop2h 04m

$177

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Fri 4/24

6:55 pm-8:23 pm

Nonstop2h 28m

Chicago O'Hare Intl

Sun 4/26

7:15 am-10:28 am

Nonstop2h 13m

$177

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Thu 5/7

5:17 am-10:16 am

1 stop5h 59m

Chicago O'Hare Intl

Sun 5/10

2:00 pm-7:29 pm

1 stop4h 29m

$197

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Mon 4/20

6:00 pm-7:10 pm

Nonstop2h 10m

Chicago Midway

Sun 4/26

7:40 am-10:35 am

Nonstop1h 55m

$197

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Mon 5/4

2:15 pm-3:25 pm

Nonstop2h 10m

Chicago Midway

Thu 5/7

3:25 pm-6:25 pm

Nonstop2h 00m

$197
Quickest round-trip

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Fri 4/17

2:00 pm-3:05 pm

Nonstop2h 05m

Chicago Midway

Mon 4/20

9:00 am-11:50 am

Nonstop1h 50m

$197

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Thu 4/16

6:00 am-7:21 am

Nonstop2h 21m

Chicago O'Hare Intl

Mon 4/20

6:15 pm-9:23 pm

Nonstop2h 08m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/5

Showing 1-10 of 60 resultsSorted by cheapest first
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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, January is the cheapest month in which you can book a flight from Maryland to Chicago (average of $57). Flying from Maryland to Chicago in June is currently the most expensive (average of $134). 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 March 6, 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 40% 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 February 21, 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. Saturday at noon 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 Maryland to Chicago?

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 28m. Fly via Frontier, United Airlines, or Delta to get the fastest option. The distance between Maryland and Chicago is about 676 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 $43 and $67 on Frontier 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 CommutAir (100%), Cathay Pacific (100%) or Royal Jordanian (92%) 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 $682, our data indicates the cheapest price to be $82. The most popular route (Washington, D.C. Dulles Intl - Chicago O'Hare Intl), is priced around $136.

  • 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, January is the cheapest month in which you can book a flight from Maryland to Chicago (average of $57). Flying from Maryland to Chicago in June is currently the most expensive (average of $134). 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 March 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$41Average$114FlexibilityNo cancel feeOn-time65%
FrontierCheapest$57Average$165FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$139Average$288FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$151Average$297FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$379FlexibilityNo cancel feeOn-time71%

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