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$41+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — CHI
nov. 26 — dic. 31
mar. 11/26
mar. 12/3
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 noviembre 21, 2024.

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 noviembre 21, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 11/21. 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.
jue. 12/54:50 pmPHL - MDW
Nonstop2h 22mFrontier
lun. 12/98:15 amMDW - PHL
Nonstop2h 03mFrontier
Deal found 11/21$76
This Cheapflightsfares deal was found by Cheapflights users on 11/21. 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.
vie. 12/610:19 pmPHL - ORD
Nonstop2h 28mFrontier
lun. 12/94:58 pmORD - PHL
Nonstop2h 07mFrontier
Deal found 11/21$77
This Cheapflightsfares deal was found by Cheapflights users on 11/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/134:33 pmBWI - MDW
Nonstop2h 04mFrontier
mié. 12/182:20 pmMDW - BWI
1 stop5h 30mFrontier
Deal found 11/20$101
This Frontier deal was found by Cheapflights users on 11/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/179:07 amBWI - ORD
1 stop8h 26mFrontier
mié. 12/186:55 amORD - BWI
1 stop6h 42mFrontier
Deal found 11/20$108
This Kiwi.com deal was found by Cheapflights users on 11/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/910:47 amBWI - ORD
1 stop5h 56mMultiple Airlines
mié. 12/111:13 pmORD - BWI
1 stop6h 13mMultiple Airlines
Deal found 11/20$144
This Frontier deal was found by Cheapflights users on 11/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/127:00 amDCA - ORD
1 stop8h 00mFrontier
lun. 12/167:25 amORD - DCA
1 stop13h 31mFrontier
Deal found 11/20$148
This CheapOair deal was found by Cheapflights users on 11/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/155:57 pmIAD - ORD
1 stop16h 57mFrontier
mié. 12/186:55 amORD - IAD
1 stop8h 33mFrontier
Deal found 11/20$148
This Frontier deal was found by Cheapflights users on 11/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/183:25 pmIAD - MDW
1 stop6h 52mFrontier
mié. 12/258:25 amMDW - IAD
1 stop5h 00mFrontier
Deal found 11/21$148
This Trip.com deal was found by Cheapflights users on 11/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/127:00 amDCA - MDW
1 stop18h 13mFrontier
dom. 12/157:15 amMDW - DCA
1 stop8h 44mFrontier
Deal found 11/20$149
This American Airlines deal was found by Cheapflights users on 11/21. 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.
jue. 12/127:20 amPHL - ORD
Nonstop2h 28mAmerican Airlines
jue. 12/1211:57 amORD - PHL
Nonstop2h 01mAmerican Airlines
Deal found 11/21$151
This eDestinos deal was found by Cheapflights users on 11/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/237:18 pmBWI - MDW
1 stop20h 53mMultiple Airlines
vie. 1/38:20 amMDW - BWI
Nonstop1h 52mMultiple Airlines
Deal found 11/20$156
This FlightHub deal was found by Cheapflights users on 11/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/99:10 pmPHL - ORD
Nonstop2h 28mMultiple Airlines
mié. 12/111:13 pmORD - PHL
1 stop19h 47mMultiple Airlines
Deal found 11/20$164

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 2,612,795 searches. Data last updated noviembre 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

vie. 12/13

10:57 pm-12:20 am

Nonstop2h 23m

Chicago Midway

lun. 12/16

8:15 am-11:18 am

Nonstop2h 03m

$76

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

vie. 12/6

10:19 pm-11:47 pm

Nonstop2h 28m

Chicago O'Hare Intl

lun. 12/9

4:58 pm-8:05 pm

Nonstop2h 07m

$77

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

vie. 12/13

4:33 pm-5:37 pm

Nonstop2h 04m

Chicago Midway

mié. 12/18

2:20 pm-8:50 pm

1 stop5h 30m

$101

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

mar. 12/17

9:07 am-4:33 pm

1 stop8h 26m

Chicago O'Hare Intl

mié. 12/18

6:55 am-2:37 pm

1 stop6h 42m

$108

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

mié. 1/8

9:25 am-10:51 am

Nonstop2h 26m

Chicago O'Hare Intl

sáb. 1/11

6:30 am-9:31 am

Nonstop2h 01m

$137

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

mié. 1/8

5:22 pm-6:40 pm

Nonstop2h 18m

Chicago O'Hare Intl

sáb. 1/11

5:50 pm-8:48 pm

Nonstop1h 58m

$137

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

mié. 1/8

10:35 am-11:45 am

Nonstop2h 10m

Chicago Midway

sáb. 1/11

6:25 pm-9:15 pm

Nonstop1h 50m

$138

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

sáb. 1/18

11:25 am-12:45 pm

Nonstop2h 20m

Chicago O'Hare Intl

mar. 1/21

4:35 pm-7:30 pm

Nonstop1h 55m

$139

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

mié. 5/7

4:15 pm-10:21 pm

1 stop7h 06m

Chicago O'Hare Intl

mar. 5/13

6:15 am-12:37 pm

1 stop5h 22m

$143

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

mar. 12/10

10:55 am-8:15 pm

1 stop10h 20m

Chicago O'Hare Intl

vie. 12/13

6:07 pm-9:14 pm

Nonstop2h 07m

$144

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

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, September is the cheapest month in which you can book a flight from Maryland to Chicago (average of $232). Flying from Maryland to Chicago in June is currently the most expensive (average of $308). 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 noviembre 21, 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 noviembre 21, 2024.

The most flights from USMD to CHI are scheduled on a Thursday (24 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 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 noviembre 21, 2024.
Get a feel of what it's like to fly with American Airlines, United Airlines and Spirit Airlines 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
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,005 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,755 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,464 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Porter Airlines
7.8
Good
288 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Air Transat
7.8
Good
389 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 $43. Users have also found prices from $66 and $69 on American Airlines 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, Baltimore/Washington - Chicago O'Hare Intl or Washington, D.C. Dulles Intl - 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%), Japan Airlines (91%) or Southwest (91%) 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 $1,084, our data indicates the cheapest price to be $89. The most popular route (Washington, D.C. Reagan-National - Chicago O'Hare Intl), is priced around $163.

  • 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, September is the cheapest month in which you can book a flight from Maryland to Chicago (average of $232). Flying from Maryland to Chicago in June is currently the most expensive (average of $308). 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 2,612,795 searches. Data last updated noviembre 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$150FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$101Average$193FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$137Average$357FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$153Average$298FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$158Average$271FlexibilityNo cancel feeOn-time63%
DeltaCheapest$176Average$256FlexibilityNo cancel feeOn-timeN/A
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