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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 7/30. 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
Sun 6/30
Sun 7/7

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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$97

Good to know

Low season

January

High season

May

Cheapest flight

$37
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly and prices are also 12% lower on average.
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 4% 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 1500 reviews
8.0Food
8.2Comfort
8.0Entertainment
8.4Boarding
8.6Crew
Airline reviews

Their announcement was not quite clear in Chinese. The rest is pretty good.

8.0 ExcellentYue, May 2024IAH - TPE
Read more about EVA Air reviews

Their announcement was not quite clear in Chinese. The rest is pretty good.

The hygiene of the bathrooms were terrible. Urine smells leaked out into the cabin and the seats were really tight, even for a petite woman like myself. Flight attendants did not go through the cabin enough to offer refreshments.

I was expecting that movie selection and food would have been better. Everything else was great.

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.

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

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.

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

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

The plane was not on time for boarding or departure or arrivals.

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

I got a one-way, last-minute nonstop flight from PDX to BWI for only $125. Yes, I got nicked $79 more for a checked suitcase and $89 more for the BIG SEAT option, but it was worth it, even with $4.50 for coffee and $10 for a snack (the latter no different than any other airline). The grand total was still less flying on any other airline.

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

My flight was cancelled!!! I had to spend 200.00 on another flight!!

Horrible, first flight delayed. They switched my connecting flight while I was en route and even though I was originally supposed to be on the flight going back home to boston, refused to let me board and told me I would have to wait for next flight that was 14 hours later. Ended up renting a car and driving 6.5 hours back home. Still getting messages about flight and it is now showing that the other flight they put me on is now canceled and I would have to wait 24 hours for the next one. I will never book with spirit again

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

9 hours of delay!! Was not able to check my luggage that I paid for!!!

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

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

My experience with frontier staff at the Denver airport was absolutely horrible. The manager on duty was even worst if was the worst experience I have ever had, I have never been treated so poorly as a customer in my life! The staff was extremely rude, eye rolls and attitude and then refusal to help me at all. I wish I could never fly frontier again that’s how horrible it was!

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Book cheap flights from Chicago to Maryland

Recent round-trip flight deals

6/11Tue
nonstopFrontier
2h 02mMDW-PHL
6/12Wed
nonstopFrontier
2h 11mPHL-MDW
$56
7/16Tue
nonstopFrontier
2h 03mMDW-PHL
7/24Wed
nonstopFrontier
2h 08mPHL-MDW
$58
9/6Fri
1 stopSpirit Airlines
9h 30mORD-BWI
9/10Tue
1 stopSpirit Airlines
11h 52mBWI-ORD
$97
8/24Sat
1 stopSpirit Airlines
4h 51mORD-BWI
8/28Wed
1 stopSpirit Airlines
7h 57mBWI-ORD
$99
7/2Tue
nonstopAmerican Airlines
2h 03mORD-BWI
7/4Thu
nonstopAmerican Airlines
2h 16mBWI-ORD
$117
8/17Sat
nonstopAmerican Airlines
1h 52mORD-BWI
8/22Thu
nonstopAmerican Airlines
2h 14mBWI-ORD
$118
7/1Mon
nonstopUnited Airlines
1h 59mORD-DCA
7/5Fri
nonstopUnited Airlines
2h 10mDCA-ORD
$169
7/3Wed
nonstopUnited Airlines
2h 02mORD-IAD
7/4Thu
nonstopUnited Airlines
2h 05mIAD-ORD
$169
6/29Sat
1 stopDelta
4h 37mMDW-BWI
7/6Sat
1 stopDelta
3h 44mBWI-MDW
$176
8/2Fri
1 stopDelta
6h 36mORD-BWI
8/4Sun
1 stopDelta
4h 11mBWI-ORD
$176

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Recent one-way flight deals

7/30Tue
nonstopFrontier
2h 03mMDW-PHL
$37
6/8Sat
nonstopFrontier
2h 01mMDW-PHL
$38
8/27Tue
1 stopSpirit Airlines
9h 39mORD-PHL
$41
7/2Tue
1 stopSpirit Airlines
9h 29mORD-PHL
$46
8/17Sat
nonstopAmerican Airlines
1h 52mORD-BWI
$59
8/29Thu
nonstopAmerican Airlines
1h 55mORD-BWI
$60
7/2Tue
nonstopUnited Airlines
1h 54mORD-DCA
$85
7/2Tue
nonstopUnited Airlines
1h 53mORD-IAD
$85
7/20Sat
1 stopDelta
4h 35mMDW-BWI
$88
6/8Sat
1 stopDelta
4h 24mMDW-PHL
$88

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Last minute flights from Chicago to Maryland

Last minute flight, train and bus deals

6/5Wed
nonstopFrontier
2h 02mORD-PHL
6/10Mon
nonstopFrontier
2h 21mPHL-ORD
$76
6/5Wed
nonstopFrontier
2h 02mORD-PHL
6/9Sun
nonstopFrontier
2h 21mPHL-ORD
$78
6/5Wed
multi-stopSpirit Airlines
26h 08mORD-BWI
6/10Mon
multi-stopSpirit Airlines
21h 06mBWI-ORD
$155
6/5Wed
multi-stopSpirit Airlines
20h 59mORD-PHL
6/11Tue
multi-stopSpirit Airlines
20h 37mPHL-ORD
$161
6/5Wed
multi-stopDelta
6h 51mORD-PHL
6/11Tue
multi-stopDelta
8h 10mPHL-ORD
$176
6/1Sat
multi-stopAmerican Airlines
4h 32mORD-PHL
6/8Sat
nonstopAmerican Airlines
2h 29mPHL-ORD
$209
6/5Wed
nonstopAmerican Airlines
1h 49mORD-DCA
6/12Wed
nonstopAmerican Airlines
2h 11mDCA-ORD
$227
6/4Tue
multi-stopDelta
5h 15mORD-PHL
6/11Tue
multi-stopDelta
8h 10mPHL-ORD
$233
6/3Mon
nonstopUnited Airlines
2h 08mORD-PHL
6/6Thu
nonstopUnited Airlines
2h 24mPHL-ORD
$260
6/3Mon
nonstopUnited Airlines
2h 08mORD-PHL
6/5Wed
nonstopUnited Airlines
2h 22mPHL-ORD
$323

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Flights to Maryland

Return flight deals:

Maryland - Chicago

Cabin classes:

$589
$523
$412
$37