$58 Find Cheap Flights from Chicago to Maryland

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 1/18. 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
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Maryland

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Maryland, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Maryland, as well as popular online travel agencies
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Flight Deals

Book Cheap Chicago to Maryland Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Maryland that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Maryland

Isnin, Jan 26 - Ahad, Feb 1
Frontier Logo
8:45 am - 11:45 am
ORD
-
BWI
2h 00mnonstop
Frontier Logo
9:20 am - 10:47 am
BWI
-
ORD
2h 27mnonstop
$82Frontier
Khamis, Apr 9 - Isnin, Apr 13
Frontier Logo
6:00 am - 9:02 am
ORD
-
BWI
2h 02mnonstop
Frontier Logo
9:57 am - 11:21 am
BWI
-
ORD
2h 24mnonstop
$83Frontier
Jumaat, Jan 23 - Selasa, Jan 27
Spirit Airlines Logo
7:20 am - 8:01 pm
ORD
-
PHL
11h 41m1 stop
Spirit Airlines Logo
1:40 pm - 9:03 pm
PHL
-
ORD
8h 23m1 stop
$102Spirit Airlines
Khamis, Jan 22 - Sabtu, Jan 24
Spirit Airlines Logo
8:43 pm - 8:47 am
ORD
-
PHL
11h 04m1 stop
Spirit Airlines Logo
8:20 am - 9:03 pm
PHL
-
ORD
13h 43m1 stop
$107Spirit Airlines
Khamis, Jan 29 - Khamis, Feb 5
Southwest Logo
9:50 am - 12:40 pm
MDW
-
BWI
1h 50mnonstop
Southwest Logo
4:25 pm - 5:35 pm
BWI
-
MDW
2h 10mnonstop
$129Southwest
Khamis, Feb 5 - Khamis, Feb 12
Southwest Logo
1:25 pm - 5:40 pm
MDW
-
BWI
3h 15m1 stop
Southwest Logo
12:40 pm - 1:50 pm
BWI
-
MDW
2h 10mnonstop
$134Southwest
Selasa, Apr 28 - Khamis, Apr 30
United Airlines Logo
11:15 am - 2:14 pm
ORD
-
DCA
1h 59mnonstop
United Airlines Logo
11:55 am - 1:15 pm
DCA
-
ORD
2h 20mnonstop
$150United Airlines
Khamis, Feb 5 - Rabu, Feb 18
United Airlines Logo
8:52 am - 11:46 am
ORD
-
IAD
1h 54mnonstop
United Airlines Logo
1:02 pm - 2:20 pm
IAD
-
ORD
2h 18mnonstop
$150United Airlines
Khamis, Feb 12 - Khamis, Feb 12
American Airlines Logo
11:50 am - 2:41 pm
ORD
-
DCA
1h 51mnonstop
American Airlines Logo
7:59 pm - 9:24 pm
DCA
-
ORD
2h 25mnonstop
$156American Airlines
Isnin, Feb 9 - Khamis, Feb 12
American Airlines Logo
12:58 pm - 3:59 pm
ORD
-
DCA
2h 01mnonstop
American Airlines Logo
8:20 am - 9:44 am
DCA
-
ORD
2h 24mnonstop
$157American Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Maryland flights

Get data-powered insights and trends into flights from Chicago to Maryland to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago to Maryland?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Maryland departing in January.

What is the cheapest Chicago to Maryland flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Maryland from Chicago found in the last 72 hours was to Baltimore, at $58 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Baltimore (BWI), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $58.

Can I save money by flying with a layover from Chicago to Maryland?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $278, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago to Maryland?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Maryland, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Maryland is August, when tickets cost $164 (return) on average. On the other hand, the most expensive months are November and January, when the average cost of round-trip tickets is $308 and $281 respectively.

What’s the cheapest day of the week to fly from Chicago to Maryland?

The average price of all round-trip flights from Chicago to Maryland clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Maryland on a Friday and more expensive on a Sunday. On your return trip to Chicago, you should consider flying back on a Friday, and avoid Mondays for better deals.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Maryland, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Maryland, you should book around 4 weeks before departure, which saves you about 55% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$55
Best time to beat the crowds but there is an average 21% increase in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Chicago O'Hare 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 from Chicago 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 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 from Chicago 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 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 from Chicago to Maryland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • 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 $332 on average. Morning departures are around 41% 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 $782.

Reviews of the top 5 airlines serving from Chicago to Maryland

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Maryland. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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 4250 reviews
7.5Entertainment
7.0Food
8.0Comfort
8.1Boarding
8.6Crew
Airline reviews

Never went on board this flight. Kayak uses Underpricer (which is a scam business) as it's "customer service provider". This customer service is a classic bait and switch "service". I Got caught in the UnderPricer Bait and switch scam. 14 hours on the phone with people from India with heavy accents and upselling me to useless products. The original sell was a flight on spirit. Then they contact me later, an say after they have my money that the flight is no good as is is only one seat for a party of two. I am still in dispute to get my money back. Went to Spirit direct and had a beautiful vacation. I should never have used Kayak and their rip off artists UnderPricer.

2.0 MediocreAnonymous, Jan 2026
SJU - BWI
Read more Southwest reviews

Never went on board this flight. Kayak uses Underpricer (which is a scam business) as it's "customer service provider". This customer service is a classic bait and switch "service". I Got caught in the UnderPricer Bait and switch scam. 14 hours on the phone with people from India with heavy accents and upselling me to useless products. The original sell was a flight on spirit. Then they contact me later, an say after they have my money that the flight is no good as is is only one seat for a party of two. I am still in dispute to get my money back. Went to Spirit direct and had a beautiful vacation. I should never have used Kayak and their rip off artists UnderPricer.

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Pretty seamless, just a tad bit late in taking off and landing.

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

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

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

it was terrible. flight was cancelled hours before the flight without a given reason and no other booking available .

Spirit Airlines has a reputation for being a terrible, cheap airline, this is why. I took a gamble on them, having never flown with them before, and the flight got cancelled. First they delayed the flight about 4 times before finally canceling it because a flight attendant didn’t show up to work that day. That’s so stupid. When I asked a ticketing agent she said that’s “company policy”. A company policy that inconveniences hundreds of passengers because a single flight attendant didn’t show is ridiculous and inefficient. I will never, ever try flying Spirit Airlines again.

We had too many delays for the crew not the plane

Spirit cancelled the flight very late last night, I was on the way to the airport when I found out

Cancelled my flight and the earliest that they are willing give me for the next flight which was 3 days later on a weekday. Only accommodation they are willing to give was $30 airline credit that will expire in 1 year

Flight was canceled, huge lines to get baggage returned. Most other airlines had delays but not widespread cancellations like Spirit.

never ever fly spirit airlines you will be screwed in the end

It was a no show, so we got put in hotels for a nite. The A320 plane was very modern and flite and crew (if a pilot shows up were fine). Price was very good.

No Tumberlence smooth flight. Try to change the menu on Snacks.

Had a issue with catching flight due to airline, was unable to board flight

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

A 630departure flight Delayed 6hours! They changed my gate, I moved to the new gate. Had our flight on the screen for 12noon departure. I go get above to eat, check screen again and the flight was gone, no notice no announcement, nothing!! They sent my bag on the flight I wasn’t on, got it back to me 3days later. Thank goodness they did refund my money but I will NEVER fly them again.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

Plane and crew on board were fine. Everything else was terrible.

The third party booking with cheapflightsfares was awful. Kayak should NOT partner with them. They sold me a bundle including seat selection and carry-on, but did not book the carry-ons with Frontier, so I’m out of pocket for $414 more while I await resolution.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

One of the worst travel experiences I've had. Had a flight scheduled with CVG to RSW on VLSWQX this morning departing at 5:30. Two individuals at the gate and one was in training. Not her fault but she didn't have the ability to check people in resulting in at least 15 families that didn't make it on the plane because they weren't checked into the system in time. When arriving at the airport to drop off our prepaid checked bags, the bag drop off agent asked if we could check our bags at the gate because of the long line. We said no problem so arrived at the gate by 5:00. They told those people that had previously paid for checked bags to stand off to the side while they let others that either didn't have a checked bag or their bag was already on the plan through. Realizing the gate workers had an issue, they either called for help or this lady showed up late for work as she didn't arrive until 5:15. The worker who had been there training the other individual and working diligently to make sure all passengers got on board. He even said that at one point all people that are currently in line are fine but asked the person in training to stand outside the ticketing area around 5:15 to notify any late travels that the flight was in boarding process and they arrrived too late. At that point, we're sill standing off to the side with our pre-paid checked bags patiently waiting. When the new lady arrived she couldn't have been more rude. It was an awful seen. Essentially they had asked for those without an assigned seat to board last, those with pre-paid checked bag stand off to the site and any traveling with a larger items that needed to be checked at the gate (such as a stroller), wait on the side. They realized that the flight needed to leave on time so the gate attendant shut the gate. So anyone without a seat assignment, those that had pre-checked bags, and the worst one I saw was a mother with two infant children was in line with use because she was asked to stand to the side because her stroller. When they shut the door to the plan they told her she could no longer get on. Her checked bags were already on the plane with her car keys in them, and the lady told her we couldn't accept anyone else on because the door was shut. She didn't even have a way to get home from the airport. Truely evil behavior. I've flown Frontier enough to know customer service is not a top priority in the company's mission, but this was an all-time low. I'm sending this after an 18 hour drive that our family just completed to Bonita Springs . I felt really bad for the lady being trained and the other individual trying to help, but when the new lady came to the gate she was truly one of the rudest individuals I've ever met. One lady had been there since 4am but because she didn't have an assigned seat they wouldn't let her on the plan.

I loved the staff on the plane. So friendly and helpful! However, there was an argument and misunderstanding by the staff and a customer at the gate, and the staff member was being unprofessional. When we arrived in Atlanta, we waited 1.5 hrs for our luggage to arrive. When I asked the airport attendant, they said Frontier had the longest wait for luggage out of any airlines, and that they could not be held responsible for the delay.

Not clean and was told I would get a great seat and it was not great at all

Everything you need to know for your flight from Chicago to Maryland

Cabin class types available on flights to Maryland

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