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Find cheap flights from Chicago to Maryland from $37

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Maryland departing on 6/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sa 6/8
Sa 6/15

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Best Maryland Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Washington, D.C.
Baltimorenonstop$52

Good to know

Low season

January

High season

March

Cheapest flight

$37
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly with an average 25% increase in price.
Flight from Chicago Midway Airport to Baltimore

FAQs - booking Maryland flights

  • How does KAYAK find such low prices on flights from Chicago 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 Chicago to Maryland.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Maryland from Chicago 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 Chicago 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 to Maryland with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago 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 to Maryland from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Maryland

  • Morning departure is around 9% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 5 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.
8.3
EVA AirOverall score based on 1529 reviews
8.2Comfort
7.9Food
8.6Crew
8.4Boarding
8.0Entertainment
Airline reviews

The type of the food requested (Asian vegetarian) was not properly met with. They have very limited snack items that may compensate for the main meals.

8.0 ExcellentAnonymous, Apr 2024TPE - JFK
Read more about EVA Air reviews

The type of the food requested (Asian vegetarian) was not properly met with. They have very limited snack items that may compensate for the main meals.

The quality of the food is pretty good. Thank you, EVA Air.

Fast and efficient boarding. Flight was on time. Service was very good for our long flight. First time flying with this airline and I would highly recommend.

Pleasant crew. Very long flight, a bit uncomfortable at times being seated, but not too bad.

No ice for the drinks. Only gave a half a cup of your beverage. Not enough water. I got very dehydrated.

Eva air is a good airline. The seats on the way to Taipei could have certainly been more comfortable, but all in all it was a pretty good experience.

Eva is one of the top airlines in Asia... but often are over priced. Finally found a reasonable rate.

My original flight was rescheduled & EVA did a good job rescheduling my flight & connecting flight.

Polite hard working crew. No complaints really. Meals were not to my liking.

Everything was fantastic! The crew really went above and beyond to make it a great flight. I felt cared for with EVA.

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Everything was good, hard to really comfortable on a flight that long.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

They seemingly have no respect for their customers, on any level. Avoid flying spirit, they will bump you to another flight without thinking twice so they can sell your seat, no joke.

One hour late taking off. Concerning, very hard landing. Uncomfortable seats with no recline. Extremely slow baggage claim. Very professional, knowledgeable flight attendants. Brand new, very clean plane.

The flight attendants were very personable, extremely friendly, and had a very good feeling of the energy around them not to mention they’re very funny and engaging. What made up for the discomfort of the seats and the fact that the plane sat for a long time on the Turmac. Not sure if the pilot was new, but the landing was very rough sort of like I was at a magic mountain theme park ride that was built in 1959

Flight was delayed 2+ hours missed a concert because of it…

I liked that bag check was rather quick and efficient. The airplane chairs on the first leg of the trip were hard and uncomfortable. Also, the cabin temperature was too cold. The lady giving seat assignments took entirely too long. She said she would call me back to the desk in 5 minutes, and she never called me back.

Seats could use more padding. Kind of hard on the tush.

The Spirit travel experience was exceptional during the peak holiday season. The flight was on time and the service was exceptional.

Turbulence Lady at ticket counter who “took care of me was completely horrible and super disrespectful And staff on plane looked like they hate their job

Amazed that Spirit can even get planes in the air, would never use again.

Crew was nasty and left the seat empty for wich I had paid rather made me sit in third class. I will never travel again in Spirit.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Book cheap flights from Chicago to Maryland

Recent round-trip flight deals

5/22Mi
nonstopFrontier
1h 50mMDW-BWI
5/29Mi
nonstopFrontier
1h 59mBWI-MDW
$52
7/10Mi
nonstopFrontier
1h 51mMDW-BWI
7/13Sa
nonstopFrontier
1h 59mBWI-MDW
$58
5/21Di
1 stopSpirit Airlines
9h 48mORD-BWI
5/29Mi
1 stopSpirit Airlines
15h 12mBWI-ORD
$88
5/28Di
1 stopSpirit Airlines
9h 48mORD-BWI
5/31Fr
1 stopSpirit Airlines
12h 43mBWI-ORD
$91
5/30Do
nonstopAmerican Airlines
2h 00mORD-BWI
7/1Mo
nonstopAmerican Airlines
2h 13mBWI-ORD
$129
5/29Mi
nonstopAmerican Airlines
2h 00mORD-BWI
6/1Sa
nonstopAmerican Airlines
2h 18mBWI-ORD
$157
5/29Mi
nonstopUnited Airlines
1h 58mORD-DCA
6/5Mi
nonstopUnited Airlines
2h 11mDCA-ORD
$169
6/5Mi
nonstopUnited Airlines
1h 55mORD-IAD
6/12Mi
nonstopUnited Airlines
2h 10mIAD-ORD
$169
7/6Sa
1 stopDelta
5h 51mMDW-BWI
7/10Mi
1 stopDelta
5h 44mBWI-MDW
$176
7/2Di
1 stopDelta
5h 45mORD-BWI
7/6Sa
1 stopDelta
4h 16mBWI-ORD
$176

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Recent one-way flight deals

6/5Mi
nonstopFrontier
1h 48mMDW-BWI
$37
7/24Mi
nonstopFrontier
1h 51mMDW-BWI
$38
6/4Di
1 stopSpirit Airlines
12h 55mORD-BWI
$45
5/29Mi
1 stopSpirit Airlines
13h 02mORD-BWI
$46
5/31Fr
nonstopUnited Airlines
2h 02mORD-BWI
$84
5/29Mi
nonstopUnited Airlines
2h 02mORD-IAD
$85
8/6Di
nonstopAmerican Airlines
2h 09mORD-DCA
$85
6/8Sa
1 stopDelta
5h 35mORD-BWI
$87
6/8Sa
1 stopDelta
4h 37mMDW-BWI
$88
8/17Sa
nonstopAmerican Airlines
1h 51mORD-DCA
$95

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Last minute flights from Chicago to Maryland

Last minute flight, train and bus deals

5/13Mo
nonstopFrontier
1h 48mMDW-BWI
5/20Mo
nonstopFrontier
1h 59mBWI-MDW
$214
5/9Do
multi-stopFrontier
5h 09mORD-BWI
5/15Mi
multi-stopFrontier
8h 41mBWI-ORD
$238
5/10Fr
multi-stopAmerican Airlines
4h 17mORD-DCA
5/10Fr
nonstopAmerican Airlines
2h 20mDCA-ORD
$285
5/13Mo
multi-stopSpirit Airlines
24h 26mORD-BWI
5/15Mi
multi-stopSpirit Airlines
13h 04mBWI-ORD
$301
5/13Mo
multi-stopSpirit Airlines
22h 47mORD-BWI
5/15Mi
multi-stopSpirit Airlines
18h 22mBWI-ORD
$317
5/9Do
nonstopAmerican Airlines
2h 00mORD-BWI
5/15Mi
nonstopAmerican Airlines
2h 18mBWI-ORD
$379
5/14Di
nonstopUnited Airlines
1h 52mORD-IAD
5/16Do
multi-stopUnited Airlines
4h 35mIAD-ORD
$380
5/13Mo
nonstopUnited Airlines
1h 52mORD-IAD
5/15Mi
nonstopUnited Airlines
2h 09mIAD-ORD
$385
5/10Fr
multi-stopDelta
5h 16mORD-IAD
5/15Mi
multi-stopDelta
5h 53mIAD-ORD
$404
5/11Sa
multi-stopDelta
4h 05mMDW-IAD
5/21Di
multi-stopDelta
4h 06mIAD-MDW
$428

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Flights to Maryland

Return flight deals:

Maryland - Chicago

Cabin classes:

$455
$769
$488
$27