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Find cheap flights from Chicago to Maryland from $33

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 7/10. 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
Tue 6/11
Tue 6/18

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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.
Baltimore1 stop$92

Good to know

Low season

January

High season

March

Cheapest flight

$33
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 23% increase in price.
Flight from Chicago Midway Airport to Philadelphia

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 12% cheaper 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 1518 reviews
8.4Boarding
7.9Food
8.2Comfort
8.6Crew
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.

Eva Air's Business Class is pretty decent. With the given price, I think that the food can be better.

Pleasant, comfortable, and entertaining. All told, ZERO issues with it. And sadly, so far the flight was WAY more comfortable than the hellhole that is "Lambug Beach Resort" at Badian Beach!

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.

I’ve had a couple flights this week on United that were delayed by an hour or more

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

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.

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

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.

Book cheap flights from Chicago to Maryland

Recent round-trip flight deals

5/21Tue
nonstopFrontier
2h 03mMDW-PHL
5/22Wed
nonstopFrontier
2h 13mPHL-MDW
$46
5/21Tue
nonstopFrontier
2h 03mMDW-PHL
5/29Wed
nonstopFrontier
2h 13mPHL-MDW
$49
6/4Tue
1 stopSpirit Airlines
9h 41mORD-PHL
6/5Wed
1 stopSpirit Airlines
11h 18mPHL-ORD
$82
5/21Tue
1 stopSpirit Airlines
13h 20mORD-PHL
5/29Wed
1 stopSpirit Airlines
11h 06mPHL-ORD
$85
5/18Sat
nonstopAmerican Airlines
2h 04mORD-PHL
5/25Sat
nonstopAmerican Airlines
2h 24mPHL-ORD
$146
6/5Wed
nonstopUnited Airlines
1h 55mORD-IAD
6/18Tue
nonstopUnited Airlines
2h 05mIAD-ORD
$169
5/30Thu
nonstopAmerican Airlines
1h 47mORD-DCA
5/30Thu
nonstopAmerican Airlines
2h 20mDCA-ORD
$169
8/2Fri
1 stopDelta
4h 23mMDW-BWI
8/10Sat
1 stopDelta
4h 38mBWI-MDW
$176
6/15Sat
1 stopDelta
4h 37mORD-BWI
6/16Sun
1 stopDelta
4h 16mBWI-ORD
$176
5/25Sat
1 stopUnited Airlines
5h 42mORD-PHL
5/27Mon
1 stopUnited Airlines
7h 03mPHL-ORD
$179

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Recent one-way flight deals

7/10Wed
nonstopFrontier
1h 59mMDW-PHL
$33
6/8Sat
nonstopFrontier
2h 01mMDW-PHL
$34
5/28Tue
1 stopSpirit Airlines
9h 48mORD-BWI
$34
5/21Tue
1 stopSpirit Airlines
9h 48mORD-BWI
$35
6/20Thu
nonstopAmerican Airlines
2h 04mORD-PHL
$66
8/17Sat
nonstopAmerican Airlines
1h 55mORD-BWI
$79
5/18Sat
nonstopUnited Airlines
2h 03mORD-PHL
$80
6/11Tue
nonstopUnited Airlines
2h 02mORD-IAD
$85
6/1Sat
1 stopDelta
4h 30mMDW-BWI
$88
7/15Mon
1 stopDelta
5h 51mMDW-PHL
$88

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Last minute flights from Chicago to Maryland

Last minute flight, train and bus deals

5/15Wed
nonstopFrontier
2h 03mMDW-PHL
5/22Wed
nonstopFrontier
2h 13mPHL-MDW
$92
5/17Fri
nonstopFrontier
2h 00mMDW-PHL
5/21Tue
nonstopFrontier
2h 21mPHL-MDW
$99
5/14Tue
multi-stopSpirit Airlines
9h 39mORD-PHL
5/21Tue
multi-stopSpirit Airlines
13h 30mPHL-ORD
$143
5/14Tue
multi-stopSpirit Airlines
9h 39mORD-PHL
5/21Tue
multi-stopSpirit Airlines
25h 21mPHL-ORD
$170
5/14Tue
nonstopAmerican Airlines
1h 56mORD-PHL
5/21Tue
nonstopAmerican Airlines
2h 23mPHL-ORD
$206
5/14Tue
nonstopAmerican Airlines
1h 53mORD-PHL
5/18Sat
nonstopAmerican Airlines
2h 24mPHL-ORD
$220
5/14Tue
multi-stopDelta
7h 09mORD-PHL
5/21Tue
multi-stopDelta
6h 19mPHL-ORD
$238
5/14Tue
nonstopUnited Airlines
2h 08mORD-PHL
5/21Tue
nonstopUnited Airlines
2h 25mPHL-ORD
$276
5/15Wed
multi-stopDelta
3h 46mORD-PHL
5/15Wed
multi-stopDelta
6h 17mPHL-ORD
$289
5/13Mon
nonstopUnited Airlines
2h 03mORD-PHL
5/18Sat
nonstopUnited Airlines
2h 25mPHL-ORD
$290

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Flights to Maryland

Return flight deals:

Maryland - Chicago

Cabin classes:

$455
$769
$488
$27