HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$60+ 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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — CHI
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Maryland to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$108
(Frontier)

One-way from

$60
(CheapOair)

Popular in

April

Cheapest in

September

Average price

$248

Good round-trip deal

$149 or less

Good one-way deal

$84 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. 8% potential increase in price ($21 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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

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 October 14, 2025.

This Frontier deal was found by Cheapflights users on 10/12. 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 11/32:35 pmPHL - ORD
1 stop9h 53mFrontier
Thu 11/63:18 pmORD - PHL
1 stop8h 01mFrontier
Deal found 10/12$108
This CheapOair deal was found by Cheapflights users on 10/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/296:50 pmPHL - MDW
1 stop15h 22mFrontier
Sat 11/11:37 pmMDW - PHL
1 stop9h 36mFrontier
Deal found 10/12$108
This Frontier deal was found by Cheapflights users on 10/13. 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 11/137:25 pmBWI - MDW
Nonstop2h 06mFrontier
Mon 11/173:40 pmMDW - BWI
Nonstop1h 55mFrontier
Deal found 10/13$108
This Frontier deal was found by Cheapflights users on 10/12. 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 11/104:30 pmBWI - ORD
1 stop8h 41mFrontier
Mon 11/175:05 amORD - BWI
1 stop9h 30mFrontier
Deal found 10/12$108
This Booking.com deal was found by Cheapflights users on 10/13. 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.
Mon 10/276:42 amPHL - ORD
1 stop19h 17mFrontier
Mon 11/311:53 amORD - PHL
1 stop11h 46mFrontier
Deal found 10/13$109
This Booking.com deal was found by Cheapflights users on 10/12. 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 10/3011:18 amPHL - MDW
1 stop28h 04mFrontier
Sat 11/111:36 amMDW - PHL
1 stop19h 54mFrontier
Deal found 10/12$109
This Mytrip deal was found by Cheapflights users on 10/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/134:15 pmBWI - ORD
1 stop8h 56mFrontier
Mon 11/1711:24 amORD - BWI
1 stop11h 49mFrontier
Deal found 10/12$109
This Frontier deal was found by Cheapflights users on 10/12. 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 10/307:25 pmBWI - MDW
Nonstop2h 06mFrontier
Thu 11/63:40 pmMDW - BWI
Nonstop1h 55mFrontier
Deal found 10/12$110
This Frontier deal was found by Cheapflights users on 10/12. 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 10/244:46 pmBWI - ORD
Nonstop2h 29mFrontier
Fri 10/3111:00 amORD - BWI
Nonstop2h 03mFrontier
Deal found 10/12$110
This Kiwi.com deal was found by Cheapflights users on 10/14. 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 10/301:19 pmPHL - MDW
Nonstop2h 14mFrontier
Sun 11/28:32 amMDW - PHL
Nonstop2h 02mFrontier
Deal found 10/14$111
This Kiwi.com deal was found by Cheapflights users on 10/13. 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.
Fri 10/247:54 pmBWI - MDW
Nonstop2h 06mFrontier
Mon 11/176:15 amMDW - BWI
1 stop8h 20mFrontier
Deal found 10/13$111
This Frontier deal was found by Cheapflights users on 10/14. 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 10/306:00 amPHL - ORD
Nonstop2h 26mFrontier
Sun 11/25:01 amORD - PHL
Nonstop2h 12mFrontier
Deal found 10/14$112

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 October 14, 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 2/11

1:10 pm-2:40 pm

Nonstop2h 30m

Chicago O'Hare Intl

Wed 2/18

2:15 pm-5:22 pm

Nonstop2h 07m

$139

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 1/7

5:45 pm-7:00 pm

Nonstop2h 15m

Chicago Midway

Sat 1/10

9:45 am-12:40 pm

Nonstop1h 55m

$139

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 11/12

4:45 pm-5:50 pm

Nonstop2h 05m

Chicago Midway

Sat 11/15

4:45 pm-7:35 pm

Nonstop1h 50m

$139

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Wed 12/10

1:15 pm-2:35 pm

Nonstop2h 20m

Chicago O'Hare Intl

Sun 12/14

11:05 am-2:07 pm

Nonstop2h 02m

$158

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Sun 12/14

6:30 am-7:56 am

Nonstop2h 26m

Chicago O'Hare Intl

Tue 12/16

6:28 pm-9:36 pm

Nonstop2h 08m

$158

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 11/13

9:55 pm-11:00 pm

Nonstop2h 05m

Chicago Midway

Sat 11/15

8:40 am-11:30 am

Nonstop1h 50m

$158

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Wed 12/3

6:30 am-7:56 am

Nonstop2h 26m

Chicago O'Hare Intl

Fri 12/5

2:30 pm-5:39 pm

Nonstop2h 09m

$158

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Fri 1/23

10:10 am-11:38 am

Nonstop2h 28m

Chicago O'Hare Intl

Sat 1/24

2:30 pm-5:34 pm

Nonstop2h 04m

$158

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Fri 11/14

6:31 pm-8:00 pm

Nonstop2h 29m

Chicago O'Hare Intl

Sat 11/15

2:20 pm-5:29 pm

Nonstop2h 09m

$158

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Wed 12/3

1:15 pm-2:35 pm

Nonstop2h 20m

Chicago O'Hare Intl

Mon 12/8

6:28 pm-9:36 pm

Nonstop2h 08m

$158

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

Showing 1-10 of 60 results
1
2
3
...
6

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 October 14, 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 62% 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 October 12, 2025.

Travelers seeking maximum savings on their Maryland to Chicago flight should consider departing on Saturday at noon when fares are most often at their lowest. Sunday 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 October 14, 2025.

The most flights from USMD to CHI are scheduled on a Monday (31 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (18 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 15m. Fly via United Airlines, Southwest, or Frontier 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 United Airlines. According to our data, you can fly for as low as $70. Users have also found prices from $70 and $70 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 Japan Airlines (92%), Royal Jordanian (89%) or ANA (89%) 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 $870, our data indicates the cheapest price to be $49. The most popular route (Washington, D.C. Reagan-National - Chicago O'Hare Intl), is priced around $108.

  • 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Maryland to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Newark to O'Hare Intl flights
Seattle to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Baltimore to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Denver to O'Hare Intl flights
Atlanta to Midway flights
Boston to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Ontario to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Orlando to O'Hare Intl flights
Hobby to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Los Angeles to Midway flights
LaGuardia to Midway flights
Tampa to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Minneapolis to Midway flights
Boston to Midway flights
Baltimore to Midway flights
San Diego to O'Hare Intl flights
Dulles Intl to Midway flights
Newark to Midway flights
Hobby to Midway flights
Austin to O'Hare Intl flights
Detroit to O'Hare Intl flights
LaGuardia to St. Louis flights
John F Kennedy Intl to St. Louis flights
Love Field to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Miami to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Pittsburgh to O'Hare Intl flights
Seattle to Midway flights
San Francisco to Midway flights
Portland to O'Hare Intl flights
Newark to St. Louis flights
Denver to Midway flights
Cleveland to O'Hare Intl flights

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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$52Average$124FlexibilityNo cancel feeOn-time65%
FrontierCheapest$68Average$170FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$328FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$157Average$291FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$158Average$307FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$164Average$311FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.