$38 Find Cheap Flights from Illinois to Maryland

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Low seasonFebruary
High seasonMay
Cheapest flight$38
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Chicago Midway Airport to Baltimore

FAQs for booking flights from Illinois to Maryland

  • How does KAYAK find such low prices on flights from Illinois to Maryland?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Illinois to Maryland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Illinois to Maryland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Illinois to Maryland is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Illinois to Maryland?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Illinois to Maryland with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Illinois to Maryland?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Illinois to Maryland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which is the cheapest airport to fly into in Maryland?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Maryland is Baltimore/Washington Airport (BWI), with an average flight price of $158.

  • What is the cheapest day to fly to Maryland?

    Based on KAYAK data, the cheapest day to fly to Maryland is Thursday where round-trip tickets can be as cheap as $299. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $433 on average.

  • What is the cheapest time of day to fly to Maryland?

    The cheapest time of day to fly to Maryland is generally in the morning, when round-trip flights cost $305 on average. Morning departures are around 23% cheaper than evening flights, on average. The most expensive time of day to fly to Maryland is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $595.

  • What is the cheapest flight to Maryland?

    The cheapest ticket to Maryland from Illinois found in the last 72 hours was to Baltimore, at $150 round-trip. The most popular route is Chicago Midway Airport (MDW) to Baltimore (BWI) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $150.

  • What is the cheapest month to fly from Illinois to Maryland?

    The cheapest month for flights from Illinois to Maryland is September, when tickets cost $246 (return) on average. On the other hand, the most expensive months are March and April, when the average cost of round-trip tickets is $329 and $317 respectively.

  • How far in advance should I book a flight from Illinois to Maryland?

    To get a below average price on the flight from Illinois to Maryland, you should book around 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

  • How long is the flight to Maryland?

    An average nonstop flight from Illinois to Maryland takes 4h 52m, covering a distance of 680 miles. The shortest route is Chicago Midway Airport (MDW) to Washington, D.C. Reagan-National Airport (DCA) with an average flight time of 1h 40m.

  • What are the most popular destinations in Maryland?

    Based on KAYAK flight searches, the most popular destination is Washington, D.C. (73% of total searches to Maryland). The next most popular destinations are Philadelphia (27%) and Salisbury (0%).

Top 5 airlines serving from Illinois to Maryland

Need help choosing which airline to fly with from Illinois 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 4293 reviews
8.6Crew
8.2Boarding
7.6Entertainment
7.1Food
8.0Comfort
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Our flight was diverted from being a non-stop to getting within 150 miles and requiring another plane. We heard 4 or 5 different versions from SW as to why we had to stop, then wait for a replacement plane. Five hour delay, weather did not come up as a single excuse.... communication was not clear and well explained. No one really took charge!

Flight was delayed due to weather. Crew did a nice job of making us comfortable. No complain complaints.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

The worst flight of my life. Never will I fly frontier again

Book cheap flights from Illinois to Maryland

Recent round-trip flight deals

5/30Fri
nonstopFrontier
1h 53mMDW-BWI
6/4Wed
nonstopFrontier
2h 04mBWI-MDW
$87
5/28Wed
nonstopFrontier
1h 53mMDW-BWI
6/4Wed
nonstopFrontier
2h 04mBWI-MDW
$88
5/23Fri
nonstopUnited Airlines
2h 03mORD-BWI
5/24Sat
nonstopUnited Airlines
2h 15mBWI-ORD
$159
6/14Sat
nonstopAmerican Airlines
2h 19mORD-BWI
6/21Sat
nonstopAmerican Airlines
2h 14mBWI-ORD
$160
6/4Wed
nonstopAmerican Airlines
2h 01mORD-BWI
6/10Tue
nonstopAmerican Airlines
2h 22mBWI-ORD
$161
6/13Fri
nonstopSouthwest
1h 45mMDW-BWI
7/5Sat
nonstopSouthwest
2h 00mBWI-MDW
$168
7/4Fri
1 stopSouthwest
4h 35mMDW-BWI
7/8Tue
nonstopSouthwest
2h 00mBWI-MDW
$169
5/24Sat
nonstopUnited Airlines
1h 57mORD-DCA
5/28Wed
nonstopUnited Airlines
2h 16mDCA-ORD
$170
6/14Sat
1 stopDelta
5h 29mMDW-BWI
6/21Sat
1 stopDelta
5h 01mBWI-MDW
$197
5/23Fri
1 stopDelta
7h 25mORD-BWI
6/1Sun
1 stopDelta
4h 51mBWI-ORD
$197

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Recent one-way flight deals

7/9Wed
nonstopFrontier
1h 58mMDW-BWI
$38
5/28Wed
nonstopFrontier
1h 53mMDW-BWI
$39
7/2Wed
nonstopUnited Airlines
2h 02mORD-BWI
$80
7/1Tue
nonstopSouthwest
1h 45mMDW-BWI
$80
5/24Sat
nonstopUnited Airlines
1h 57mORD-DCA
$81
7/1Tue
nonstopSouthwest
1h 55mMDW-PHL
$81
7/1Tue
nonstopAmerican Airlines
2h 09mORD-PHL
$81
6/4Wed
nonstopAmerican Airlines
2h 04mORD-PHL
$89
5/23Fri
1 stopDelta
5h 17mMDW-BWI
$99
7/1Tue
1 stopDelta
5h 03mMDW-PHL
$99

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Last minute flights from Illinois to Maryland

Last minute flight, train and bus deals

5/5Mon
multi-stop
6h 04mORD-BWI
5/12Mon
multi-stop
11h 38mBWI-ORD
$200
5/5Mon
multi-stopFrontier
6h 04mORD-BWI
5/10Sat
multi-stopFrontier
7h 56mBWI-ORD
$208
5/2Fri
multi-stopUnited Airlines
16h 37mORD-IAD
5/3Sat
nonstopUnited Airlines
2h 14mIAD-ORD
$392
5/3Sat
nonstopUnited Airlines
1h 56mORD-IAD
5/3Sat
multi-stopUnited Airlines
19h 40mIAD-ORD
$422
5/4Sun
nonstopSouthwest
2h 00mMDW-PHL
5/7Wed
nonstopSouthwest
2h 10mPHL-MDW
$474
5/4Sun
multi-stopSouthwest
8h 00mMDW-PHL
5/7Wed
nonstopSouthwest
2h 10mPHL-MDW
$484
5/6Tue
nonstopAmerican Airlines
2h 00mORD-PHL
5/8Thu
nonstopAmerican Airlines
2h 26mPHL-ORD
$501
5/6Tue
multi-stopAmerican Airlines
3h 55mORD-PHL
5/7Wed
nonstopAmerican Airlines
2h 28mPHL-ORD
$511
5/3Sat
multi-stopDelta
4h 27mMDW-PHL
5/7Wed
multi-stopDelta
3h 24mPHL-MDW
$521
5/3Sat
multi-stopDelta
5h 07mORD-IAD
5/7Wed
multi-stopDelta
3h 57mIAD-ORD
$559

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Everything you need to know for your flight to Maryland

Cabin class types available on flights to Illinois

Cabin classes available on flights to Illinois. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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