$85 Find Cheap Flights from Chicago to Maryland - Compare and Save

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Price, demand and travel trends for Chicago to Maryland flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What are the cheapest fares from Chicago to Maryland recently?

The cheapest fare from Chicago to Maryland in the last week was $176 round-trip, to Baltimore/Washington (BWI).

How do fares into airports in Maryland compare?

According to KAYAK data from the last 12 months, the cheapest airports to fly into Maryland from Chicago are:

• Baltimore/Washington (BWI) (avg. price $295)
• Salisbury-Ocean City (SBY) (avg. price $670)

Are flights from Chicago to Maryland cheaper or more expensive than last year?

Fares from Chicago to Maryland are about 24% higher than they were in November last year, averaging $315 round-trip.

What's the cheapest month to fly from Chicago to Maryland?

January is typically the cheapest month to fly from Chicago to Maryland, with round-trip fares averaging $192. July and June are usually the most expensive, averaging $367 and $358, respectively.

How do fares from Chicago to Maryland vary by day of the week?

On average, Thursday is the cheapest day to fly from Chicago to Maryland and Monday is the most expensive. Looking at the past 12 months of KAYAK data, it's 27% more expensive to fly on a Monday compared to Thursday.

What's the best time of day to fly from Chicago to Maryland?

It's cheapest to fly to Maryland in the afternoon with average prices of $290. The night is the most expensive time to fly, with average prices of $347.

What's the best time to book a flight from Chicago to Maryland?

Book your flights 21 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 57% compared to booking at the last minute (within 2 weeks of departure).

Key details for Chicago to Maryland flights

Low season

March

Cheapest flight

$85
Beat the crowds with an average 11% drop in travelers.
The most popular month to fly with an average 13% increase in travelers.
One-way flight from Chicago O'Hare Intl Airport to Baltimore

Your Chicago to Maryland flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Chicago to Maryland?

    Yes. Fares from Chicago to Maryland are low right now. As a rule of thumb, a round-trip under $196 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Chicago to Maryland?

    Over the past 12 months, round-trip fares from Chicago to Maryland have typically cost between $196 and $406.

  • What are the main airports serving Maryland?

    Maryland has 9 airports. 100% of KAYAK users choose Baltimore/Washington (BWI) as their arrival airport.

  • Which airlines fly nonstop from Chicago to Maryland?

    Based on the flight schedule for the next 3 months, 4 airlines offer nonstop flights on this route:

    • Southwest
    • American Airlines
    • United Airlines
    • Frontier

  • Which destinations in Maryland can I fly nonstop from Chicago?

    Based on the flight schedule for the next 3 months, you can fly nonstop from Chicago to just one destination in Maryland: Baltimore.

  • Is it cheaper to fly with a layover from Chicago to Maryland?

    Yes, nonstop flights from Chicago to Maryland average $302 over the past 12 months, but flights with a layover can cost less. The most affordable connecting airports are:

    • Fort Lauderdale (FLL) (avg. price $191)
    • Orlando (MCO) (avg. price $196)
    • Miami (MIA) (avg. price $206)

  • How long is a flight from Chicago to Maryland?

    Nonstop flights from Chicago to Maryland take 2h 01m on average. All flights fly into Baltimore/Washington (BWI).

  • Which cabin classes are available from Chicago to Maryland?

    On flights from Chicago to Maryland you can book Economy Class, Business Class or First Class.

  • What are some popular landmarks around Maryland?

    Maryland is home to many popular sights. KAYAK travelers' favorites include:

    • M&T Bank Stadium
    • National Aquarium Baltimore
    • Oriole Park At Camden Yards
    • Pier Six Pavilion

  • What are the earliest and latest flights from Chicago to Maryland?

    The earliest nonstop flight from Chicago to Maryland departs at 5:05 am and the latest leaves at 9:36 pm. Nonstop flights take about 2h 01m.

Your guide to booking Chicago to Maryland flights

Get tips on when to book, when to fly and what to know before your trip.
  • If you can plan ahead, the sweet spot for booking your flight is 21 weeks before your trip. KAYAK data shows fares in this window are around 57% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • Flexible with your dates? Fly in January to save some money. It's typically the cheapest month on this route, while flights in July will cost you the most.
  • Fly out on a Thursday to get the cheapest fares. Avoid Monday flights, which are about 27% more expensive.
  • If you're watching your budget, fly into Baltimore/Washington (BWI) which has the lowest average airfare in the region. Just remember to budget for any onward travel by bus, car or domestic flight.
  • Start your trip in Ocean City, the most popular destination in Maryland. From there, it's easy to continue on to other popular spots such as Baltimore, Annapolis and National Harbor.
  • Whether you're trying to save time or money, Baltimore/Washington (BWI) is usually your best option from Chicago.

Reviews of the top 4 airlines serving from Chicago to Maryland

 
Need help choosing which airline to fly with from Chicago to Maryland? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4220 reviews
8.6Crew
7.5Entertainment
8.0Comfort
8.1Boarding
7.0Food
Airline reviews

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

8.0 ExcellentEmmalee, Oct 2026
Read more Southwest reviews

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

Southwest’s point to point system caused a 2 hour delay due to the crew being late from their inbound flight. Also, the WiFi and entertainment didn’t work on the plane.

A) Checked my luggage at the gate but never got to pre board B) if we are helping with checking our carryon and waiting 40 minutes for it we should have some privileges c) luggage took 40-45 minutes to come.. d) I asked for another snack and was told the plane is full.. seriously a small snack

I like the staff members they were super nice and helpful very sweet people :)

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Very uncomfortable and cramped seats. Everything else was okay, the crew members were nice but nothing was exceptional.

Waited on tarmac for approximately 15-25 minutes before taking off. When landing, the time it took to taxi to our gate was the also 15-25 minutes.

Connection times always good online, but not in reality when first leg is delayed (2 out of 2 times this trip).

It was good flight was smooth, little cold on the plane but other wise good.

Great flight and crew. Need more legroom and DO NOT allow seats to recline.

The guy in front of me was talking constantly, even when the pilot was making announcements. I found this very disrespectful to the pilot and to others.

The TVs on the plane were all broken and inoperable. No snacks or food were served. Plane was very old and uncomfortable.

Takeoff delayed 2 hrs. Boarded on time to find we were missing part of the flight crew. Then informed that they had loaded too much fuel. Spent 1 1/2 hrs sitting there burning off the excess, which included a couple of laps around the runway until we were light enough to fly! Ridiculous!

I especially enjoyed having a lightly packed flight which enabled me and my wife to occupy a three seat area with nobody in the middle seat.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

All good. Flight crew was super friendly at the end of a long day

The food in first class has taken a big downturn

Flight was fine. Just delays leaving due to mechanical issues. But flight crew were kind and professional. Seats were spacious. American doesn't need to have 9 groups for boarding.

Both departure and return flights had mechanical delays. Their planes are antiquated resulting in a two hour flight taking almost four hours to complete.

Crew were helpful, pilot kept us informed about turbulence, snack choice was awesome!

It was one of the worst I have ever had. The plane was over booked, and I did not have a seat. When I questioned why because I had booked this weeks in advance. I was brushed off to be advised they are trying to find someone to give up their seat. Only to be advised I would be boarding last. I had priority boarding in group 1-4. When I asked why I had to be last because that is not what I paid for I was advised it doesn't matter you will get a seat. The ticket person was very rude and unprofessional. The gate changed several times and it was going from one area to another area far away from where we were at. I feel like I should have been compensated in some kind of way because of the way I was treated. The ticket agent acted like it was my fault that the plane was over booked. Not one time was I apologized to for this inconvenience.

I have posted the comments in the first flight leg.

First class snacks - stewardess gave out multiples to everyone until there was almost no selection left when she got back to me last in first class cabin. Nothing left that I would eat.

My feedback from the trip to Columbia to Chicago was meant for Chicago to Denver.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

More options for your flight from Chicago to Maryland

Complete your trip to Maryland with a hotel stay or car rental