HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$94+ 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 7/3. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — CHI
Jul 6 — Jul 131
Mon 7/6
Mon 7/13
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

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 June 6, 2026.

This Expedia deal was found by Cheapflights users on 6/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:06 pm
PHL
-
ORD
Nonstop2h 41m
Multiple Airlines
Fri 7/1010:56 am
ORD
-
PHL
1 stop8h 04m
Multiple Airlines
Deal found 6/3$199
This Kiwi.com deal was found by Cheapflights users on 6/3. 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.
Thu 8/2011:35 am
PHL
-
ORD
1 stop9h 54m
Frontier
Sat 8/227:52 pm
ORD
-
PHL
Nonstop2h 28m
Frontier
Deal found 6/3$200
This Frontier deal was found by Cheapflights users on 6/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/236:05 pm
PHL
-
ORD
Nonstop2h 42m
Frontier
Sat 8/18:52 pm
ORD
-
PHL
Nonstop2h 23m
Frontier
Deal found 6/2$201
This Kiwi.com deal was found by Cheapflights users on 6/5. 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.
Fri 8/146:11 pm
PHL
-
ORD
Nonstop2h 42m
Frontier
Sat 8/227:52 pm
ORD
-
PHL
Nonstop2h 28m
Frontier
Deal found 6/5$202
This Frontier deal was found by Cheapflights users on 6/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/116:05 pm
PHL
-
ORD
Nonstop2h 42m
Frontier
Thu 7/168:52 pm
ORD
-
PHL
Nonstop2h 23m
Frontier
Deal found 6/4$203
This CheapOair deal was found by Cheapflights users on 6/4. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:06 pm
PHL
-
ORD
Nonstop2h 41m
Multiple Airlines
Wed 7/810:56 am
ORD
-
PHL
1 stop8h 04m
Multiple Airlines
Deal found 6/4$204
This Super.com deal was found by Cheapflights users on 6/5. 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 7/186:05 pm
PHL
-
ORD
Nonstop2h 42m
Frontier
Thu 7/235:13 pm
ORD
-
PHL
1 stop6h 38m
Frontier
Deal found 6/5$205
This Frontier deal was found by Cheapflights users on 6/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:06 pm
PHL
-
ORD
Nonstop2h 41m
Frontier
Sun 9/67:52 pm
ORD
-
PHL
Nonstop2h 28m
Frontier
Deal found 6/4$206
This Super.com deal was found by Cheapflights users on 6/4. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/206:11 pm
PHL
-
ORD
Nonstop2h 42m
Frontier
Thu 7/238:52 pm
ORD
-
PHL
Nonstop2h 23m
Frontier
Deal found 6/4$207
This Frontier deal was found by Cheapflights users on 6/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/186:05 pm
PHL
-
ORD
Nonstop2h 42m
Frontier
Mon 7/207:05 am
ORD
-
PHL
1 stop11h 15m
Frontier
Deal found 6/4$208
This Kiwi.com deal was found by Cheapflights users on 6/3. 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 8/54:30 pm
PHL
-
MDW
1 stop6h 33m
Frontier
Thu 8/2012:27 pm
MDW
-
PHL
1 stop5h 50m
Frontier
Deal found 6/3$208
This Kiwi.com deal was found by Cheapflights users on 6/3. 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 8/58:30 am
PHL
-
ORD
1 stop12h 23m
Frontier
Tue 8/181:50 pm
ORD
-
PHL
1 stop7h 39m
Frontier
Deal found 6/3$210

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 June 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$199
(Expedia)

One-way from

$94
(Super.com)

Popular in

March

Cheapest in

September

Average price

$309

Good round-trip deal

$318 or less

Good one-way deal

$183 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. 6% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 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

Thu 9/10

6:00 am-1:20 pm

1 stop8h 20m

Chicago O'Hare Intl

Mon 9/14

2:15 pm-10:32 pm

1 stop7h 17m

$219

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Tue 9/29

11:20 am-1:50 pm

1 stop3h 30m

Chicago Midway

Thu 10/1

5:00 pm-7:45 pm

Nonstop1h 45m

$227

BaltimoreChicago

BWI - RFD

BWIRFD

Baltimore/Washington

Sat 7/25

1:05 pm-10:37 am

1 stop22h 32m

Chicago Greater Rockford

Sun 8/2

11:27 am-12:10 pm

1 stop23h 43m

$230

PhiladelphiaChicago

PHL - RFD

PHLRFD

Philadelphia

Wed 6/17

8:00 am-10:37 am

1 stop27h 37m

Chicago Greater Rockford

Sun 6/28

11:27 am-12:44 am

1 stop12h 17m

$239

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 8/19

9:39 am-1:13 pm

1 stop4h 34m

Chicago O'Hare Intl

Sat 8/22

10:50 am-7:34 pm

1 stop7h 44m

$241

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 8/4

6:10 am-9:17 am

1 stop4h 07m

Chicago Midway

Sat 8/8

6:42 pm-11:26 pm

1 stop3h 44m

$241

BaltimoreChicago

BWI - RFD

BWIRFD

Baltimore/Washington

Sat 7/11

1:05 pm-10:37 am

1 stop22h 32m

Chicago Greater Rockford

Mon 7/13

7:50 pm-8:54 am

1 stop12h 04m

$242

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Tue 7/7

1:00 pm-4:10 pm

1 stop4h 10m

Chicago Midway

Sat 7/11

5:00 am-7:45 am

Nonstop1h 45m

$245

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 7/11

5:42 pm-6:50 pm

Nonstop2h 08m

Chicago O'Hare Intl

Tue 7/14

11:07 am-2:12 pm

Nonstop2h 05m

$247
Quickest round-trip

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Tue 7/21

8:30 pm-9:40 pm

Nonstop2h 10m

Chicago Midway

Thu 7/23

7:00 am-9:45 am

Nonstop1h 45m

$253

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/2

Showing 1-10 of 60 resultsSorted by cheapest first
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, February is the cheapest month in which you can book a flight from Maryland to Chicago (average of $43). Flying from Maryland to Chicago in July is currently the most expensive (average of $623). 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 June 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 afternoon, which can drop the price by up to 33% versus a flight in the morning.

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 June 6, 2026.

The most flights from USMD to CHI are scheduled on a Friday (36 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (10 on average).

How much does it cost to fly round-trip from Maryland to Chicago?

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

Booking 67 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 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 30, 2026.

Travelers seeking maximum savings on their Maryland to Chicago flight should consider departing on Friday at noon 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.

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 3h 30m. Fly via JetBlue, Southwest, or Delta 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 Frontier. According to our data, you can fly for as low as $43. Users have also found prices from $61 and $69 on Southwest and American Airlines, 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 Japan Airlines (86%), Qatar Airways (83%) or United Airlines (83%) 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 $859, our data indicates the cheapest price to be $116. The most popular route (Baltimore/Washington - Chicago O'Hare Intl), is priced around $138.

  • 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, February is the cheapest month in which you can book a flight from Maryland to Chicago (average of $43). Flying from Maryland to Chicago in July is currently the most expensive (average of $623). 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

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.
Newark to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Seattle to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Hobby to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Denver to O'Hare Intl flights
Ontario to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Newark to Midway flights
Boston to O'Hare Intl flights
Orlando to O'Hare Intl flights
Atlanta to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Tampa to O'Hare Intl flights
Los Angeles to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Dulles Intl to Midway flights
Fort Lauderdale to O'Hare Intl flights
Miami to O'Hare Intl flights
Austin to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
San Francisco to Midway flights
Charlotte to O'Hare Intl flights
San Diego to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Atlanta to Midway flights
LaGuardia to Midway flights
Baltimore to Midway flights
Minneapolis to Midway flights
Minneapolis to O'Hare Intl flights
Reagan-National to Midway flights
San Jose to O'Hare Intl flights
Hobby to Midway flights
Denver to Midway flights
Burbank to O'Hare Intl flights
Hartford to O'Hare Intl flights
Philadelphia to Midway flights
Portland to O'Hare Intl flights
Salt Lake City to O'Hare Intl flights
Las Vegas to O'Hare Intl flights
Newark to St. Louis flights
Kansas City to O'Hare Intl flights

Top 4 airlines flying from Maryland to Chicago

Discover the top 4 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 June 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$57Average$167FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$122Average$287FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$153Average$325FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$308FlexibilityNo 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.
Site
©2026 Cheapflights