$99 Find Cheap Flights from Chicago to Maryland - Compare and Save

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 7/28. 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.
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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

Sat, Aug 15 - Mon, Aug 17
Multiple Airlines Logo
8:52 pm - 12:15 am
ORD
-
PHL
2h 23mnonstop
Multiple Airlines Logo
6:33 pm - 12:50 pm
PHL
-
ORD
19h 17m
2 stops
$206Multiple Airlines
Fri, Jul 31 - Thu, Aug 6
Frontier Logo
1:50 pm - 10:33 pm
ORD
-
PHL
7h 43m
1 stop
Frontier Logo
6:05 pm - 7:47 pm
PHL
-
ORD
2h 42mnonstop
$207Frontier
Thu, Jul 30 - Thu, Aug 6
Frontier Logo
8:52 pm - 12:15 am
ORD
-
PHL
2h 23mnonstop
Frontier Logo
6:05 pm - 7:47 pm
PHL
-
ORD
2h 42mnonstop
$208Frontier
Sat, Aug 8 - Mon, Aug 10
Southwest Logo
8:05 am - 3:00 pm
MDW
-
DCA
5h 55m
1 stop
Southwest Logo
1:00 pm - 5:50 pm
DCA
-
MDW
5h 50m
2 stops
$236Southwest
Sat, Oct 10 - Thu, Oct 15
American Airlines Logo
8:58 pm - 11:59 pm
ORD
-
DCA
2h 01mnonstop
American Airlines Logo
6:00 am - 7:27 am
DCA
-
ORD
2h 27mnonstop
$236American Airlines
Sat, Jul 25 - Sat, Aug 1
Southwest Logo
5:55 am - 8:40 am
MDW
-
DCA
1h 45mnonstop
Southwest Logo
6:10 am - 7:10 am
DCA
-
MDW
2h 00mnonstop
$237Southwest
Mon, Aug 3 - Sat, Aug 8
American Airlines Logo
8:55 pm - 11:59 pm
ORD
-
DCA
2h 04mnonstop
American Airlines Logo
5:23 pm - 6:54 pm
DCA
-
ORD
2h 31mnonstop
$237American Airlines
Sat, Jul 25 - Sat, Aug 8
Delta Logo
7:05 am - 11:28 am
ORD
-
DCA
3h 23m
1 stop
Delta Logo
10:10 am - 4:51 pm
DCA
-
ORD
7h 41m
1 stop
$238Delta
Sat, Aug 8 - Sat, Aug 15
Delta Logo
6:42 pm - 10:59 pm
MDW
-
DCA
3h 17m
1 stop
Delta Logo
6:30 pm - 10:36 pm
DCA
-
MDW
5h 06m
1 stop
$238Delta
Wed, Jul 29 - Fri, Jul 31
United Airlines Logo
2:00 pm - 5:12 pm
ORD
-
DCA
2h 12mnonstop
United Airlines Logo
1:00 pm - 2:18 pm
DCA
-
ORD
2h 18mnonstop
$243United 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 September.

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 5 days was to Baltimore, at $193 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 5 days was $193.

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 $400 on average. Morning departures are around 32% 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 $770.

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 $355, 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 February, when tickets cost $27 (return) on average. On the other hand, the most expensive months are October and June, when the average cost of round-trip tickets is $549 and $161 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 Thursday, 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 49% 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$99
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 34% lower on average.
Flight from Chicago O'Hare Airport to Reagan Washington National Airport

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 4 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.
7.9
SouthwestOverall score based on 4250 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

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.

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

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

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

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

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

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 !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

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

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

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.