Cheap flights from Maryland to Chicago from $58
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Maryland to Chicago departing on 10/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Southwest flights from Maryland to Chicago Midway Airport
Our best Southwest deals on Maryland to Chicago Midway Airport flight tickets
Frontier flights from Maryland to Chicago Midway Airport
Our best Frontier deals on Maryland to Chicago Midway Airport flight tickets
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How to get the cheapest flight ticket from Maryland to Chicago Midway Airport
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Chicago Midway Airport?
The month of February is, on average, the cheapest month to fly to Chicago Midway Airport from Maryland, with most prices found around $181. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Maryland during the month September is also very affordable. Most momondo users find prices during this month for around $186.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Maryland. The lowest ticket price found for a Wednesday departure recently was $329. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Maryland because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $402.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Maryland in the evening is the least expensive time of day to depart. momondo users have found prices as low as $319 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $357. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Maryland to Chicago Midway flight route?
Fly from Baltimore/Washington to Chicago Midway for the best Maryland - Chicago Midway flight prices
How far in advance should I book a flight to Chicago Midway Airport?
You are more likely to see cheaper flights to Chicago Midway Airport from Maryland when booking 12 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $230 when searching 12 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Maryland for as low as $151 on momondo.
What cabin class options are available on Maryland to Chicago Midway flights?
There are 1 cabin classes available to choose from on Maryland to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Maryland to Chicago Midway?
Frontier, Southwest, and Allegiant Air are the most popular carriers operating from Maryland to Chicago Midway
What airlines fly to Chicago Midway Airport?
Frontier, Southwest and Delta are the top three most popular airlines that fly to Chicago Midway Airport from Maryland according to our data. Frontier is the first choice among our users, with 50% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 3 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Maryland to Chicago Midway Airport on average per day?
The number of flights available between Maryland and Chicago Midway Airport is 16 per day as of June 2025. The most frequent departure time is 6:00PM, with 39% of daily flights leaving in the afternoon.
How many flights depart from Maryland to Chicago Midway Airport on average per week?
As of June 2025, there are 118 flights per week flying from Maryland to Chicago Midway Airport. The most common day of the week flights depart is Mon, with 20% of flights taking off on this day.
Cheap Maryland to Chicago Midway Airport flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Maryland to Chicago Midway Airport
When did momondo last update prices for flights from Maryland to Chicago Midway Airport?
Prices for flights from Maryland to Chicago Midway Airport were last updated today.
How many operators does momondo search for flights from Maryland to Chicago Midway Airport?
The number of operators available for flights from Maryland to Chicago Midway Airport is 4 as of June 2025.
How old do you have to be to fly from Maryland to Chicago Midway Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Maryland to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Maryland to Chicago Midway Airport?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Maryland to Chicago Midway Airport is Boeing 737-800 Passenger/BBJ2 (winglets) (12.63% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (11.62%), Boeing 737-700 Passenger/BBJ1 (winglets) (10.53%), and Airbus A320neo (10.09%).
Best airlines flying from Maryland to Chicago Midway Airport
Compare and see reviews for airlines that fly from Maryland to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $58 | Free Cancellation | Rating 5.9 3,295 reviews | |||
| PriceFrom $98 | Free Cancellation | Rating 8.0 7,946 reviews | |||
| PriceFrom $171 | Free Cancellation | Rating 8.0 4,287 reviews |
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Maryland to Chicago?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Maryland.
Can I find flights from Maryland to Chicago with flexible booking policies on momondo?
momondo does allow users to show only those flights to Chicago from Maryland which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Maryland to Chicago?
Once you have performed a search for Maryland to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.
I’m not ready to book a flight from Maryland to Chicago right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Maryland and alert you when they change.