Cheap flights from Maryland to Chicago from $39
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 5/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Maryland to Chicago
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
Spirit Airlines flights from Maryland to Chicago
Our best Spirit Airlines deals on Maryland to Chicago flight tickets
Delta flights from Maryland to Chicago
Our best Delta deals on Maryland to Chicago flight tickets
See travel insights to Chicago from
How to get the cheapest flight ticket from Maryland to Chicago
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?
The month of September is, on average, the cheapest month to fly to Chicago from Maryland, with most prices found around $209. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Maryland to Chicago during January average around $229.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $402. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Maryland to Chicago for around $495.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Maryland to Chicago during this time can be as low as $337. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $456.
What is the cheapest Maryland to Chicago flight route?
Fly from Baltimore/Washington to Chicago Midway for the best Maryland - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from Maryland when booking 6 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $335 when searching 6 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Maryland for as low as $266 on momondo.
What cabin class options are available on Maryland to Chicago flights?
There are 4 cabin classes available to choose from on Maryland to Chicago 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?
Frontier, Spirit Airlines, and Southwest are the most popular carriers operating from Maryland to Chicago
What airlines fly to Chicago?
United Airlines, Southwest and American Airlines are the top three most popular airlines that fly to Chicago from Maryland according to our data. United Airlines is the first choice among our users, with 37% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Maryland to Chicago on average per day?
As of April 2025, 85 flights take off from Maryland and land in Chicago each day. The most common flight departure time for this route is 10:00AM, with 64% of daily flights taking off at noon.
How many flights depart from Maryland to Chicago on average per week?
As of April 2025, 597 flights take off from Maryland and land in Chicago each week. The most common flight departure day for this route is Wed, with 27% of weekly flights taking off on this day.
Cheap Maryland to Chicago flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Maryland to Chicago
When did momondo last update prices for flights from Maryland to Chicago?
Prices for flights from Maryland to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from Maryland to Chicago?
There are 6 operators available for flights from Maryland to Chicago as of April 2025.
How old do you have to be to fly from Maryland to Chicago?
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.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Maryland to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Maryland to Chicago is Boeing 737 MAX 8, representing 9.54% of all bookings. The subsequent popular models are Boeing 737-800 Passenger/BBJ2 (winglets) at 9.44%, Airbus A319 at 9.05%, and Airbus A320-100/200 at 7.62%.
Best airlines flying from Maryland to Chicago
Compare and see reviews for airlines that fly from Maryland to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $56 | Free Cancellation | Rating 6.3 7,963 reviews | |||
| PriceFrom $58 | Free Cancellation | Rating 5.9 3,287 reviews | |||
| PriceFrom $98 | Free Cancellation | Rating 8.0 7,934 reviews | |||
| PriceFrom $142 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $154 | Free Cancellation | Rating 7.4 8,696 reviews | |||
| PriceFrom $167 | Free Cancellation | Rating 8.0 4,294 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?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Maryland to Chicago. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from Maryland to Chicago with flexible booking policies on momondo?
Yes. All flights to Chicago from Maryland on momondo can be compared and filtered by various policies on offer, including flexible booking.
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?
Of course. momondo tracks the price of Maryland to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.