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$92+ 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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — CHI
Jun 3 — Jun 101
Wed 6/3
Wed 6/10
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 May 4, 2026.

This Frontier deal was found by Cheapflights users on 4/29. 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.
Tue 6/308:30 am
PHL
-
ORD
1 stop12h 23m
Frontier
Mon 7/68:05 pm
ORD
-
PHL
Nonstop2h 26m
Frontier
Deal found 4/29$184
This Trip.com deal was found by Cheapflights users on 4/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:30 am
PHL
-
MDW
1 stop5h 39m
Frontier
Sat 5/306:00 am
MDW
-
PHL
1 stop5h 25m
Frontier
Deal found 4/29$184
This Frontier deal was found by Cheapflights users on 4/29. 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.
Sun 5/105:13 pm
PHL
-
ORD
Nonstop2h 38m
Frontier
Fri 5/227:52 pm
ORD
-
PHL
Nonstop2h 26m
Frontier
Deal found 4/29$185
This Frontier deal was found by Cheapflights users on 4/30. 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.
Wed 6/31:30 pm
PHL
-
MDW
1 stop9h 32m
Frontier
Wed 6/1012:04 pm
MDW
-
PHL
1 stop9h 25m
Frontier
Deal found 4/30$185
This Super.com deal was found by Cheapflights users on 4/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/115:06 pm
PHL
-
ORD
Nonstop2h 38m
Frontier
Sat 5/161:59 pm
ORD
-
PHL
1 stop7h 11m
Frontier
Deal found 4/30$186
This Frontier deal was found by Cheapflights users on 4/30. 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.
Thu 5/144:35 pm
PHL
-
MDW
1 stop6h 27m
Frontier
Sun 5/246:00 am
MDW
-
PHL
1 stop5h 25m
Frontier
Deal found 4/30$186
This Super.com deal was found by Cheapflights users on 5/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/55:06 pm
PHL
-
ORD
Nonstop2h 38m
Frontier
Fri 6/128:00 pm
ORD
-
PHL
Nonstop2h 32m
Frontier
Deal found 5/2$187
This Frontier deal was found by Cheapflights users on 4/30. 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.
Thu 6/45:06 pm
PHL
-
ORD
Nonstop2h 38m
Frontier
Sat 6/68:00 pm
ORD
-
PHL
Nonstop2h 27m
Frontier
Deal found 4/30$188
This Super.com deal was found by Cheapflights users on 5/1. 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 6/115:06 pm
PHL
-
ORD
Nonstop2h 41m
Frontier
Sat 6/138:00 pm
ORD
-
PHL
Nonstop2h 32m
Frontier
Deal found 5/1$189
This Super.com deal was found by Cheapflights users on 4/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:06 pm
PHL
-
ORD
Nonstop2h 38m
Frontier
Mon 5/117:52 pm
ORD
-
PHL
Nonstop2h 26m
Frontier
Deal found 4/30$190
This Frontier deal was found by Cheapflights users on 4/30. 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.
Tue 7/76:30 am
PHL
-
MDW
1 stop5h 37m
Frontier
Tue 7/216:00 am
MDW
-
PHL
1 stop5h 22m
Frontier
Deal found 4/30$190
This Frontier deal was found by Cheapflights users on 4/29. 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.
Sun 5/105:13 pm
PHL
-
ORD
Nonstop2h 38m
Frontier
Wed 6/179:13 pm
ORD
-
PHL
1 stop11h 03m
Frontier
Deal found 4/29$191

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 May 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$184
(Frontier)

One-way from

$92
(Trip.com)

Popular in

April

Cheapest in

September

Average price

$293

Good round-trip deal

$309 or less

Good one-way deal

$176 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. 15% potential increase in price ($47 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 4, 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

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 5/27

6:05 am-8:45 am

1 stop3h 40m

Chicago O'Hare Intl

Sat 5/30

11:09 am-5:27 pm

1 stop5h 18m

$228

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 5/23

4:24 pm-9:46 pm

1 stop6h 22m

Chicago O'Hare Intl

Tue 5/26

6:07 am-12:18 pm

1 stop5h 11m

$228

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 6/3

12:40 pm-4:56 pm

1 stop5h 16m

Chicago O'Hare Intl

Thu 6/4

7:07 am-2:10 pm

1 stop6h 03m

$228

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 5/23

4:24 pm-9:09 pm

1 stop5h 45m

Chicago Midway

Tue 5/26

6:36 pm-10:56 pm

1 stop3h 20m

$228

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 6/1

6:00 am-8:43 am

1 stop3h 43m

Chicago Midway

Wed 6/3

6:36 pm-10:56 pm

1 stop3h 20m

$228

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 6/6

6:05 am-8:43 am

1 stop3h 38m

Chicago Midway

Wed 6/10

1:26 pm-6:59 pm

1 stop4h 33m

$228

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 6/16

6:30 am-7:46 am

Nonstop2h 16m

Chicago O'Hare Intl

Thu 6/18

6:00 am-8:54 am

Nonstop1h 54m

$233
Quickest round-trip

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 6/6

6:10 am-7:10 am

Nonstop2h 00m

Chicago Midway

Wed 6/10

5:05 pm-7:55 pm

Nonstop1h 50m

$233

BaltimoreChicago

BWI - RFD

BWIRFD

Baltimore/Washington

Tue 7/21

5:33 pm-9:13 am

1 stop16h 40m

Chicago Greater Rockford

Sun 7/26

11:27 am-12:15 pm

1 stop23h 48m

$240

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Fri 6/26

8:16 am-9:30 am

Nonstop2h 14m

Chicago O'Hare Intl

Tue 6/30

9:20 pm-12:28 am

Nonstop2h 08m

$243

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

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

How far ahead should I book a flight from Maryland to Chicago?

Booking 68 days in advance of your planned departure date is, on average, the best time to get cheap flights from Maryland to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, May is the cheapest month in which you can book a flight from Maryland to Chicago (average of $34). Flying from Maryland to Chicago in August is currently the most expensive (average of $701). 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 May 4, 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 afternoon, which can drop the price by up to 31% 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 May 2, 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.

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 May 4, 2026.

The most flights from USMD to CHI are scheduled on a Sunday (36 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (14 on average).

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. Fly via Delta, United Airlines, or Southwest to get the fastest option. The distance between Maryland and Chicago is about 599 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 $43. Users have also found prices from $43 and $63 on Frontier and Southwest, respectively.

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

    Most travelers choose Baltimore/Washington - Chicago O'Hare Intl, Washington, D.C. Dulles Intl - 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 Qatar Airways (85%), Japan Airlines (80%) or Republic Airways (80%) 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 $663, our data indicates the cheapest price to be $100. The most popular route (Baltimore/Washington - Chicago O'Hare Intl), is priced around $134.

  • 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, May is the cheapest month in which you can book a flight from Maryland to Chicago (average of $34). Flying from Maryland to Chicago in August is currently the most expensive (average of $701). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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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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LaGuardia to Midway flights
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Reagan-National to Midway flights
Fort Lauderdale to O'Hare Intl flights
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Denver to Midway flights
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Minneapolis to O'Hare Intl flights
Los Angeles to Midway flights
Miami to O'Hare Intl flights
LaGuardia to St. Louis flights
Newark to St. Louis flights
Love Field to O'Hare Intl flights
Tampa to Midway flights
Minneapolis to Midway flights
Burbank to O'Hare Intl flights
George Bush Intcntl to Midway flights

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 May 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$43Average$118FlexibilityNo cancel feeOn-time65%
FrontierCheapest$57Average$164FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$134Average$293FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$152Average$311FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$415FlexibilityNo cancel feeOn-time71%

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