To save up to 65% on this flight, we recommend booking at least 43 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Maryland to Chicago from $396 1-2 weeks out and tickets from $451 for flights departing within the next 72 hours.
Due to multiple factors, expect to potentially pay more when booking in June. For low rates, January can be a great choice for travel to Chicago. Flights to Chicago from Maryland in January are about $300 on average during January, but can be found for as low as $94.
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.
Fly from
Fly to
Budget
$58 - $119
Route
Depart
Return
Price
Baltimore/WashingtonChicago Midway
BWI - MDW
BWIMDW
Baltimore/Washington
Wed 6/5
Nonstop1h 59m
Chicago Midway
Sat 6/8
Nonstop1h 50m
Baltimore/WashingtonChicago Midway
BWI - MDW
BWIMDW
Baltimore/Washington
Wed 6/5
Nonstop1h 59m
Chicago Midway
Sat 6/8
Nonstop1h 50m
Baltimore/WashingtonChicago Midway
BWI - MDW
BWIMDW
Baltimore/Washington
Wed 5/15
Nonstop2h 03m
Chicago Midway
Wed 5/22
Nonstop1h 50m
Baltimore/WashingtonChicago O'Hare Intl
BWI - ORD
BWIORD
Baltimore/Washington
Wed 5/15
1 stop11h 51m
Chicago O'Hare Intl
Tue 5/21
1 stop9h 48m
Baltimore/WashingtonChicago Midway
BWI - MDW
BWIMDW
Baltimore/Washington
Wed 5/15
Nonstop2h 03m
Chicago Midway
Fri 5/17
Nonstop1h 50m
Baltimore/WashingtonChicago O'Hare Intl
BWI - ORD
BWIORD
Baltimore/Washington
Tue 5/14
1 stop12h 09m
Chicago O'Hare Intl
Tue 5/21
1 stop9h 48m
Baltimore/WashingtonChicago O'Hare Intl
BWI - ORD
BWIORD
Baltimore/Washington
Wed 5/15
1 stop8h 41m
Chicago O'Hare Intl
Tue 5/21
1 stop9h 48m
Baltimore/WashingtonChicago Midway
BWI - MDW
BWIMDW
Baltimore/Washington
Fri 5/17
Nonstop1h 59m
Chicago Midway
Mon 5/20
Nonstop1h 50m
Baltimore/WashingtonChicago O'Hare Intl
BWI - ORD
BWIORD
Baltimore/Washington
Thu 5/30
Nonstop2h 18m
Chicago O'Hare Intl
Fri 5/31
Nonstop2h 00m
No data available for this route at this time. Please check back soon.
Overall
Comfort
Boarding
Food
Entertainment
Crew
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Overall
Comfort
Boarding
Food
Entertainment
Crew
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Overall
Comfort
Boarding
Food
Entertainment
Crew
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Overall
Comfort
Boarding
Food
Entertainment
Crew
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Overall
Comfort
Boarding
Food
Entertainment
Crew
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Overall
Comfort
Boarding
Food
Entertainment
Crew
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
13%of flight departures | Early morningMidnight to 6 am |
---|---|
37%of flight departures | Morning6 am to noon |
42%of flight departures | AfternoonNoon to 6 pm |
8%of flight departures | Evening6 pm to midnight |
Cheapflights helps you search for flights from Maryland to Chicago via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.
By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from Maryland.
Certainly. Search results for flights to Chicago from Maryland shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.
Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!