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Cheap flights from Maryland (MD) to Chicago (CHI)

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How to find the cheapest flight from
Maryland to Chicago (CHI)

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

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 20 days in advance, which can save you up to 48% on flights from Maryland to Chicago compared to booking the week you need them. Waiting 20 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $213. For sooner than that we have options available in the next 3 days from $293.

What is the cheapest month to fly from Maryland to Chicago?

Our data shows that August tends to be the cheapest month to fly to Chicago from Maryland. Users have commonly found prices around $182 for the month, but tickets can be as low as $64. Due to multiple factors, prepare for potentially higher prices in December.

Cheap flights from Maryland to Chicago in November, December 2020

The best prices found for Maryland to CHI flights for November, December
20 Dec - 9 Jan
$54pp
BWI
Baltimore/Washington
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BWI
Baltimore/Washington
19 Dec - 20 Jan
$60pp
BWI
Baltimore/Washington
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BWI
Baltimore/Washington
11 Dec - 17 Dec
$62pp
BWI
Baltimore/Washington
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
BWI
Baltimore/Washington

Maryland to Chicago 2021 flight deals

Cheap flights to Chicago from Maryland found for next year
20 Dec - 9 Jan
$54pp
BWI
Baltimore/Washington
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BWI
Baltimore/Washington
19 Dec - 20 Jan
$60pp
BWI
Baltimore/Washington
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BWI
Baltimore/Washington
11 Dec - 17 Dec
$62pp
BWI
Baltimore/Washington
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
BWI
Baltimore/Washington

Non-stop flights to Chicago from Maryland

Save time with Maryland to Chicago direct flight deals
16 Jan - 17 Jan
$40pp
BWI
Baltimore/Washington
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BWI
Baltimore/Washington
26 Feb - 1 Mar
$41pp
BWI
Baltimore/Washington
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BWI
Baltimore/Washington
8 Jan - 11 Jan
$49pp
BWI
Baltimore/Washington
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BWI
Baltimore/Washington

Last minute flights from Maryland to Chicago

Late deals on round-trip flights to Chicago from Maryland, departing today and this week
10 Dec - 14 Dec
$79pp
BWI
Baltimore/Washington
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BWI
Baltimore/Washington
9 Dec - 16 Dec
$82pp
BWI
Baltimore/Washington
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BWI
Baltimore/Washington
7 Dec - 12 Dec
$98pp
BWI
Baltimore/Washington
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BWI
Baltimore/Washington

One-way flights to Chicago from Maryland

The cheapest one-way flights from Maryland to Chicago
9:00 am - 5:25 pm
Spirit Airlines
1 Stop
9h 25m
BWI - ORD
Spirit Airlines
$59
CheapTickets.com
2:47 pm - 12:06 pm
Frontier
1 Stop
22h 19m
BWI - ORD
Frontier
$60
Kiwi.com
2:30 am - 1:03 am
Multiple Airlines
2 Stops
23h 33m
BWI - ORD
Multiple Airlines
$62
Gotogate

Related info for your journey

Useful info, stats and facts about Maryland to Chicago flights.

Flight FAQs

From Maryland to Chicago

Are flight prices decreasing from Maryland to Chicago due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Maryland and Chicago for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

What safety measures are being taken by airlines flying from Maryland to Chicago to control the spread of COVID-19?

Airlines globally have implemented additional safety measures to accommodate you. JetBlue, Southwest, and Delta are some of the many airlines that have done so. Some of the new policies that have been implemented to accommodate travelers flying from Maryland to Chicago are improved sanitation, HEPA filters, mask requirements, social distance seating (for a limited time), and pre-flight testing for antibodies and symptoms. Policies will vary by airline.

Which airlines flying from Maryland to Chicago have flexible cancellations due to COVID-19?

Some of our airline partners flying from Maryland to Chicago have new flexible policies in place due to COVID-19. United Airlines, American Airlines, and Spirit Airlines are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like United Airlines with this kind of flexibility.

Can I find flights from Maryland to Chicago for under $100 on Cheapflights?

Yes, there are multiple flights from Maryland to Chicago for under $100. The cheapest flight booked recently is on Spirit Airlines for just $40, but on average you can expect to pay $61.

Are there nonstop flights from Maryland to Chicago for under $100 on Cheapflights?

Cheapflights has at least 20 direct flights from Maryland to Chicago under $100. A good price for a nonstop flight from Maryland to Chicago is less than $81.

Are there last-minute flights available from Maryland to Chicago for under $100?

There are currently 20+ open flights from Maryland to Chicago within the next 7 days for less than $100.

What are the most popular airlines that fly from Maryland to Chicago?

When booking a flight from Maryland to Chicago, you may want to consider flying on Major Airline, American Airlines or JetBlue as they are the most popular for this route.

What are the most popular routes from Maryland to Chicago?

While some choose either Washington Dulles Intl - Chicago O'Hare Intl or Baltimore/Washington - Chicago O'Hare Intl, Washington Reagan-National - Chicago O'Hare Intl is the most popular route from Maryland to Chicago.

What are the cheapest Flights from Maryland to Chicago?

Looking at all options, your cheapest flight can be booked for $50. While the most popular route (Washington Reagan-National - Chicago O'Hare Intl) can be booked for $123 on average our data indicates $153 when flying from Maryland to Chicago

What are the most reliable airlines from Maryland to Chicago?

Before booking your flight to Chicago from Maryland, check out the most reliable airlines to get you to your destination on time: Iberia (100%), Republic Airways (100%), ANA( 99%).

How long is the flight from Maryland to Chicago?

There are many flights that can get you from Maryland to Chicago in 1h 56m. Fly via Spirit Airlines, United Airlines, or Delta to get the fastest option. Both multi-stop and nonstop flights can be found to your destination and back.

What are the cheapest airlines flying from Maryland to Chicago round-trip?

Cheapflights users have booked flights from Maryland to Chicago round-trip from $40. Other airlines that can offer you cheap pricing are Frontier, from $68, and United Airlines, from $71.

What are the cheapest airlines to fly from Maryland to Chicago one-way?

The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $20. Check flights for Frontier, as they currently have the next best price.

Destination information for Chicago

Things to know before you go. Useful info for your trip from Maryland to Chicago
Flight duration
1h 55m
Average temperature for November in Chicago
51.8 °F
Avg rainfall for November in Chicago
2.4 ″

Airports servicing

Frederick (FDK)
Hagerstown (HGR)
Cumberland (OBT)
Salisbury (SBY)

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 5 airlines from Maryland to Chicago

The chart below displays the airlines Cheapflights users traveling from Maryland to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.

Airline Cheapest Average Flexibility On-time COVID-19 safety
Spirit Airlines
$56 $189 No cancel fee 65%
Delta
$72 $235 No cancel fee N/A
United Airlines
$67 $247 No cancel fee 69%
American Airlines
$51 $289 No cancel fee 71%
Southwest
$198 $418 No cancel fee 63%
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