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$53+ 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 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — CHI
Dec 27 — Jan 31
Fri 12/27
Fri 1/3
1 adult, Economy
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Cheap flight deals from Maryland to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Maryland (USMD) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 22, 2024.

Round-trip from

$108
(Frontier)

One-way from

$53
(Mytrip)
From Maryland to Chicago (CHI)
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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 December 22, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 12/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3111:43 amPHL - MDW
Nonstop2h 26mFrontier
Fri 1/34:01 pmMDW - PHL
Nonstop2h 04mFrontier
Deal found 12/21$164
This Frontier deal was found by Cheapflights users on 12/22. 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 12/311:23 pmPHL - ORD
1 stop6h 51mFrontier
Thu 1/910:35 amORD - PHL
1 stop7h 27mFrontier
Deal found 12/22$178
This Frontier deal was found by Cheapflights users on 12/22. 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 12/2510:07 amBWI - MDW
Nonstop2h 04mFrontier
Mon 2/104:08 pmMDW - BWI
Nonstop1h 55mFrontier
Deal found 12/22$184
This Mytrip deal was found by Cheapflights users on 12/22. 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.
Mon 12/309:58 pmBWI - ORD
1 stop15h 48mFrontier
Sat 1/44:45 pmORD - BWI
1 stop13h 52mFrontier
Deal found 12/22$211
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 12/311:23 pmPHL - ORD
1 stop6h 51mMultiple Airlines
Wed 1/83:31 pmORD - PHL
1 stop8h 08mMultiple Airlines
Deal found 12/22$238
This Frontier deal was found by Cheapflights users on 12/22. 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 12/304:42 pmIAD - MDW
1 stop7h 32mFrontier
Fri 1/38:25 amMDW - IAD
1 stop11h 40mFrontier
Deal found 12/22$258
This Delta deal was found by Cheapflights users on 12/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/312:45 pmPHL - ORD
1 stop9h 07mDelta
Tue 1/75:45 amORD - PHL
1 stop5h 19mDelta
Deal found 12/20$267
This United Airlines deal was found by Cheapflights users on 12/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/256:15 amPHL - ORD
2 stops6h 44mUnited Airlines
Wed 12/252:30 pmORD - PHL
Nonstop2h 06mUnited Airlines
Deal found 12/20$308
This American Airlines deal was found by Cheapflights users on 12/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/317:30 amBWI - ORD
Nonstop2h 23mAmerican Airlines
Sun 1/58:15 amORD - BWI
Nonstop2h 07mAmerican Airlines
Deal found 12/21$320
This Mytrip deal was found by Cheapflights users on 12/21. 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.
Tue 12/317:18 pmBWI - ORD
2 stops18h 11mMultiple Airlines
Sun 1/51:24 pmORD - BWI
3 stops29h 12mMultiple Airlines
Deal found 12/21$330
This Southwest deal was found by Cheapflights users on 12/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/316:40 amBWI - ORD
1 stop9h 20mSouthwest
Sun 1/54:00 pmORD - BWI
Nonstop1h 55mSouthwest
Deal found 12/21$331
This Delta deal was found by Cheapflights users on 12/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/316:05 amBWI - ORD
1 stop4h 16mDelta
Sat 1/47:05 amORD - BWI
1 stop4h 55mDelta
Deal found 12/22$340

Find flights from Maryland to Chicago within your budget

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 December 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Thu 2/6

1:41 pm-10:27 pm

1 stop9h 46m

Chicago O'Hare Intl

Wed 2/12

8:33 am-4:11 pm

1 stop6h 38m

$108

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Tue 2/11

8:47 pm-7:07 am

1 stop11h 20m

Chicago Midway

Sat 2/15

4:19 pm-12:56 am

1 stop7h 37m

$108

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Thu 1/9

4:34 pm-10:42 pm

1 stop7h 08m

Chicago O'Hare Intl

Mon 1/13

5:43 pm-9:10 am

1 stop14h 27m

$116

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Fri 1/17

4:49 pm-6:01 pm

Nonstop2h 12m

Chicago Midway

Mon 1/20

4:08 pm-7:03 pm

Nonstop1h 55m

$117

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 1/22

5:22 pm-6:40 pm

Nonstop2h 18m

Chicago O'Hare Intl

Tue 1/28

5:50 pm-8:48 pm

Nonstop1h 58m

$139

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Tue 2/4

11:51 am-1:12 pm

Nonstop2h 21m

Chicago O'Hare Intl

Wed 2/5

6:00 pm-9:03 pm

Nonstop2h 03m

$141

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Thu 1/9

1:41 pm-10:42 pm

1 stop10h 01m

Chicago O'Hare Intl

Tue 1/14

2:02 pm-10:16 pm

1 stop7h 14m

$145

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 1/15

6:10 am-7:30 am

Nonstop2h 20m

Chicago Midway

Wed 1/22

5:05 pm-7:50 pm

Nonstop1h 45m

$150

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 1/15

12:35 pm-2:00 pm

Nonstop2h 25m

Chicago O'Hare Intl

Wed 1/22

4:35 pm-7:30 pm

Nonstop1h 55m

$150

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 1/22

5:00 pm-11:32 pm

1 stop7h 32m

Chicago O'Hare Intl

Thu 1/30

6:50 am-2:22 pm

1 stop6h 32m

$152

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

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.

Travel insights for flights from Maryland to Chicago

Get recent, data-driven insights about flights from Maryland to Chicago including ideal travel times, pricing trends, and more.

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

Currently, August is the cheapest month in which you can book a flight from Maryland to Chicago (average of $245). Flying from Maryland to Chicago in March is currently the most expensive (average of $317). 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 December 22, 2024.

When flying from Maryland to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 December 22, 2024.

The most flights from USMD to CHI are scheduled on a Monday (25 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated December 22, 2024.
Get a feel of what it's like to fly with JetBlue, Frontier and Southwest from Maryland to Chicago by reading reviews from past customers. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,804 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,804 reviews
Southwest
8.1
Very good
4,804 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,549 reviews
Southwest
8.1
Very good
4,804 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,594 reviews
Southwest
8.1
Very good
4,804 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Qatar Airways
7.5
Good
3,789 reviews
Southwest
8.1
Very good
4,804 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,265 reviews
Southwest
8.1
Very good
4,804 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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.

  • 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 $53. Users have also found prices from $70 and $70 on Southwest and United Airlines, 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 ANA (97%), Southwest (94%) or Japan Airlines (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 $957, our data indicates the cheapest price to be $104. The most popular route (Washington, D.C. Dulles Intl - Chicago O'Hare Intl), is priced around $188.

  • 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, August is the cheapest month in which you can book a flight from Maryland to Chicago (average of $245). Flying from Maryland to Chicago in March is currently the most expensive (average of $317). 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

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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 December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$155FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$101Average$193FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$136Average$351FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$152Average$300FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$160Average$286FlexibilityNo cancel feeOn-time63%
DeltaCheapest$176Average$266FlexibilityNo cancel feeOn-timeN/A
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