$91 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 4/15. 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

Fri, Apr 24 - Tue, Apr 28
Frontier Logo
6:49 pm - 8:51 pm
MDW
-
BWI
25h 02m
1 stop
Frontier Logo
12:17 pm - 7:31 pm
BWI
-
MDW
8h 14m
1 stop
$147Frontier
Fri, May 8 - Tue, May 12
Frontier Logo
4:05 pm - 5:07 pm
ORD
-
BWI
24h 02m
1 stop
Frontier Logo
4:31 pm - 11:01 pm
BWI
-
ORD
7h 30m
1 stop
$147Frontier
Fri, Apr 17 - Mon, Apr 20
Multiple Airlines Logo
7:15 pm - 9:15 am
ORD
-
BWI
13h 00m
1 stop
Multiple Airlines Logo
4:10 pm - 5:36 pm
BWI
-
ORD
2h 26mnonstop
$148Multiple Airlines
Fri, Apr 17 - Sat, Apr 18
Frontier Logo
12:42 pm - 3:47 pm
ORD
-
BWI
2h 05mnonstop
Frontier Logo
6:53 am - 11:33 am
BWI
-
ORD
5h 40m
1 stop
$149Frontier
Wed, Apr 29 - Sat, May 2
Multiple Airlines Logo
1:27 pm - 9:17 am
ORD
-
BWI
18h 50m
1 stop
Multiple Airlines Logo
5:53 pm - 10:23 am
BWI
-
ORD
17h 30m
1 stop
$150Multiple Airlines
Mon, Apr 27 - Mon, May 4
Multiple Airlines Logo
11:28 am - 11:22 am
ORD
-
BWI
22h 54m
1 stop
Multiple Airlines Logo
4:24 pm - 11:58 pm
BWI
-
ORD
8h 34m
1 stop
$151Multiple Airlines
Thu, Apr 30 - Fri, May 1
Frontier Logo
1:27 pm - 9:37 am
ORD
-
BWI
19h 10m
1 stop
Frontier Logo
9:46 pm - 9:17 pm
BWI
-
ORD
24h 31m
1 stop
$152Frontier
Tue, Apr 28 - Tue, May 5
Southwest Logo
7:00 am - 9:50 am
MDW
-
BWI
1h 50mnonstop
Southwest Logo
6:30 am - 7:35 am
BWI
-
MDW
2h 05mnonstop
$177Southwest
Wed, Apr 22 - Sat, Apr 25
Southwest Logo
1:55 pm - 6:40 pm
MDW
-
DCA
3h 45m
1 stop
Southwest Logo
6:40 am - 7:45 am
DCA
-
MDW
2h 05mnonstop
$214Southwest
Wed, Apr 29 - Tue, May 5
American Airlines Logo
9:55 am - 12:55 pm
ORD
-
DCA
2h 00mnonstop
American Airlines Logo
1:48 pm - 4:36 pm
DCA
-
ORD
3h 48m
1 stop
$218American 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 April.

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 $134 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 $134.

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

The average price for all round-trip flights from Chicago to Maryland depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Maryland is generally in the morning, when round-trip flights cost $365 on average. Morning departures are around 37% 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 $806.

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 $303, 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 March, when the average cost of round-trip tickets is $308 and $300 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 50% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$91
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly and prices are also 3% 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.

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 4334 reviews
8.0Comfort
8.1Boarding
7.0Food
7.5Entertainment
8.6Crew
Airline reviews

I am very please with the service received from Southwest. Although there was a refuel stop in Fl before we got the Baltimore. The service and kindness of the staff was excellent.

8.0 ExcellentLauren, Mar 2026
SJO - BWI
Read more Southwest reviews

I am very please with the service received from Southwest. Although there was a refuel stop in Fl before we got the Baltimore. The service and kindness of the staff was excellent.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

I liked it better when you were truer to your roots Am paying more for less fun

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

The last 3 flights between BWI and BDL canceled the beverage service mid- way. Just say up front that the fight is too short. Thanks!

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

Awful. No counter attendants. No dinner offered due to delays.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

They cancelled our flight. 2 hours before we were supposed to take off and offered us nothing! We got our money back and that was it. No other flight to get to our cruise no working with another airline or with us to get there. Terrible customer service, no apology.

we boarded the plane and then sat for OVER AN HOUR on it, first waiting for fuel and then the crew timed out. the flight kept getting delayed longer and longer, a 9:30pm flight is still on the ground at 1:15am.

Delay due to personnel issues on Spirit’s end. Original departure time 9:30pm. Took off at 2:15am. Lost an entire night’s sleep bc Spirit couldn’t get a crew together. Very poor.

We get stuck in the plane when landed during 45min and no communication from the crew People were listening to their phone and music out loud and nobody told them anything I definitely want stop booking spirit flight it is a disaster

Good: It was cheap and they got us to our destination safely. Not so Good: Gates experience with many, many nauseatingly (almost) threatening announcements about bags size and how much they were going to charge us if our bag was too big, even to the point of having a gate agent roaming around through the passengers eyeballing bags size and making people go check their bags in the sizers.

Terrible. The flight was randomly delayed in Chicago causing us to miss our connection and they offered us a flight the next day at 6 am and it would have taken till 345 to get to Pensacola. They didn’t cover any fees. Our bags also supposedly were on the flight to Pensacola and we tried to get them yesterday after driving 6 hours and nobody was available. Worst company ever and will never use them again. Had to pay for a rental. Spirit is claiming in climate weather for the delay but there wasn’t any weather issuesz it’s a bunch of bullshit and I am not happy

Checking in at desk in Chicago was horrible. Person was not friendly never smiled and said my flight was not paid for so I had to give another credit card. Then it ended up that I was charged twice. Then after arriving at my destination had to wait on the phone a long time to speak to a person to fix the double charge! Thank goodness the flight was perfect.

They charged late fees for selecting seats (no $0 options). They also changed my gate within the last half hour and are refusing to reimburse my costs to drive across the country with two small children in a rental car.

Flight was delayed for 12 h. They should stop overlooking flights.

the fligh was delay form 9am to 10, delayed again from 10 to 11, than delay and gate change to 12 and delay another gate change to 3;25 pm

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

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.