Cheap flights from Chicago to Maryland from $38
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Maryland 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.
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How to get the cheapest flight ticket from Chicago to Maryland
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 Maryland?
The cheapest month to fly to Maryland from Chicago is in September. Flight prices, which tend to average around $199, are often lower during this time because this is during the off-season. If you don’t want to visit Maryland in September, then you should wait until August to fly from Chicago, when ticket prices are also cheap, with an average price of $203.
What is the cheapest day to depart on your flight to Maryland?
The cheapest day to depart from Chicago to Maryland is on a Thursday. Travelers who choose to depart for Maryland on a Thursday will often find tickets for as low as $299. The most expensive day to fly to Maryland is Monday, with ticket prices averaging around $433.
What is the cheapest time of day to depart on your flight to Maryland?
Our most recent data shows that the best time of day to fly to Maryland is in the morning. Flights from Chicago to Maryland during this time can be as low as $305. In contrast, the most expensive time of day to depart to Maryland is at noon when prices are around $595.
What is the cheapest Chicago to Maryland flight route?
Fly from Chicago Midway to Baltimore/Washington for the best Chicago - Maryland flight prices
How far in advance should I book a flight to Maryland?
You are more likely to see cheaper flights to Maryland from Chicago when booking 4 weeks ahead of your departure date. In general, you can expect to find flights to Maryland for around $307 when searching 4 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Maryland from Chicago for as low as $240 on momondo.
What cabin class options are available on Chicago to Maryland flights?
There are 4 cabin classes available to choose from on Chicago to Maryland 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 Chicago to Maryland?
Frontier, Spirit Airlines, and Southwest are the most popular carriers operating from Chicago to Maryland
What airlines fly to Maryland?
United Airlines, Southwest and American Airlines are the top three most popular airlines that fly to Maryland from Chicago according to our data. United Airlines is the first choice among our users, with 39% of people opting to fly with this airline when traveling to Maryland. Keep in mind that there are 6 different airlines that fly to Maryland on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to Maryland on average per day?
As of April 2025, there are 124 flights per day flying from Chicago to Maryland. The most common time of day flights depart is 6:00PM, with 44% of flights taking off in the evening.
How many flights depart from Chicago to Maryland on average per week?
872 flights are operational weekly from Chicago to Maryland as of April 2025. The most popular departure day for this route is Fri, with 18% of flights per week taking off on this day.
Cheap Chicago to Maryland flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Maryland
When did momondo last update prices for flights from Chicago to Maryland?
Prices for flights from Chicago to Maryland were last updated today.
How many operators does momondo search for flights from Chicago to Maryland?
The number of operators available for flights from Chicago to Maryland is 6 as of April 2025.
How old do you have to be to fly from Chicago to Maryland?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Maryland.
What documentation or ID do you need to fly to Maryland?
The travel and health documents required for your trip to Maryland 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 Maryland. 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 Chicago to Maryland?
Based on momondo bookings for flights between Chicago and Maryland, the leading plane model is Airbus A319, making up 11.62% of the total bookings. Other popular models include Boeing 737-700 Passenger/BBJ1 (winglets) with 11.10%, Boeing 737 MAX 8 with 10.16%, and Boeing 737-800 with 9.96%.
Best airlines flying from Chicago to Maryland
Compare and see reviews for airlines that fly from Chicago to Maryland with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $68 | Free Cancellation | Rating 5.9 3,283 reviews | |||
| PriceFrom $101 | Free Cancellation | Rating 6.3 7,942 reviews | |||
| PriceFrom $122 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $140 | Free Cancellation | Rating 8.0 4,287 reviews | |||
| PriceFrom $173 | Free Cancellation | Rating 7.4 8,685 reviews | |||
| PriceFrom $176 | Free Cancellation | Rating 8.0 7,920 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Maryland?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Maryland for you.
Can I find flights from Chicago to Maryland with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Maryland from Chicago with this policy.
How can momondo help me find flights from Chicago to Maryland?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Maryland from Chicago.
I’m not ready to book a flight from Chicago to Maryland right now. Can momondo alert me if prices change?
If you are not ready to book a flight from Chicago to Maryland now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Maryland and let you know when they change.