Menu

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

Know your dates, get live prices in seconds:

From
To
Depart
Return
Any month
Compare vs. Cheapflights |
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime

We work with more than 300 partners to bring you better travel deals

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 37 days in advance, which can save you up to 10% on flights from Maryland to Chicago compared to booking the week you need them. Waiting 37 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 $177. For sooner than that we have options available in the next 3 days from $177.

Cheap flights from Maryland to Chicago in September, October 2020

The best prices found for Maryland to CHI flights for September, October
9 Oct - 14 Oct
$78pp
BWI
Baltimore/Washington
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BWI
Baltimore/Washington
15 Oct - 19 Oct
$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
10 Oct - 25 Oct
$81pp
BWI
Baltimore/Washington
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BWI
Baltimore/Washington

Maryland to Chicago 2020 flight deals

Cheap flights to Chicago from Maryland found for this year
7 Nov - 14 Nov
$48pp
BWI
Baltimore/Washington
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BWI
Baltimore/Washington
10 Dec - 14 Dec
$50pp
BWI
Baltimore/Washington
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BWI
Baltimore/Washington
7 Nov - 14 Nov
$51pp
BWI
Baltimore/Washington
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BWI
Baltimore/Washington

Non-stop flights to Chicago from Maryland

Save time with Maryland to Chicago direct flight deals
7 Nov - 14 Nov
$48pp
BWI
Baltimore/Washington
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BWI
Baltimore/Washington
10 Dec - 14 Dec
$50pp
BWI
Baltimore/Washington
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BWI
Baltimore/Washington
7 Nov - 9 Nov
$51pp
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
1 Oct - 5 Oct
$99pp
BWI
Baltimore/Washington
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
BWI
Baltimore/Washington
29 Sep - 6 Oct
$108pp
BWI
Baltimore/Washington
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
BWI
Baltimore/Washington
1 Oct - 10 Oct
$115pp
BWI
Baltimore/Washington
Spirit 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
7:56 am - 9:13 am
Major Airline
Nonstop
2h 17m
BWI - ORD
Major Airline
$74
StudentUniverse
10:10 am - 6:39 pm
Spirit Airlines
1 Stop
9h 29m
BWI - ORD
Spirit Airlines
$76
Priceline
2:10 am - 12:25 pm
Delta
2 Stops
11h 15m
BWI - ORD
Delta
$79
Delta

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.

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 $48, but on average you can expect to pay $71.

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 $80.

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 Washington Reagan-National - Chicago O'Hare Intl, Baltimore/Washington - 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 (Baltimore/Washington - Chicago O'Hare Intl) can be booked for $48 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: Royal Jordanian (100%), ANA (97%), Iberia( 94%).

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 or Major Airline to get the fastest option. Generally, flights for this route are nonstop.

What is the cheapest airline to fly from Maryland to Chicago round-trip?

Cheapflights users have booked flights from Maryland to Chicago round-trip from $48.

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 $25. However, be on the lookout for offers from British Airways and Delta, as they are both options that can get you from Maryland to Chicago for a low price.

Destination information for Chicago

Things to know before you go. Useful info for your trip from Maryland to Chicago
Flight duration
2h 04m
Average temperature for September in Chicago
77.0 °F
Avg rainfall for September in Chicago
2.4 ″

Airports servicing

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

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)
Home North America USA Illinois Chicago Cheap flights from Maryland to Chicago