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Cheap flights from Chicago to Maryland from $28

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Maryland departing on 3/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago to Maryland

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Maryland that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Maryland.

Cheap last minute flights

Planning a quick getaway from Chicago to Maryland? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Maryland, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Maryland

Find recent round-trip train or bus tickets from Chicago to Maryland.

All round-trip flight deals from Chicago to Maryland

The cheapest plane tickets from Chicago to Maryland found on KAYAK recently.
10:26 am - 1:21 pmMDW-BWI
1h 55mnonstop
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
$53Frontier
Find Deal
Sat, Feb 22 - Wed, Feb 26
10:26 am - 1:21 pmMDW-BWI
1h 55mnonstop
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
$54Frontier
Find Deal
Sat, Feb 22 - Wed, Feb 26
7:00 am - 9:55 amORD-BWI
1h 55mnonstop
8:55 pm - 10:20 pmBWI-ORD
2h 25mnonstop
$148Southwest
Find Deal
Wed, Feb 19 - Wed, Feb 26
8:15 am - 11:10 amORD-BWI
1h 55mnonstop
6:07 pm - 7:29 pmBWI-ORD
2h 22mnonstop
$149American Airlines
Find Deal
Wed, Mar 5 - Tue, Mar 11
4:00 pm - 6:50 pmORD-BWI
1h 50mnonstop
8:55 pm - 10:20 pmBWI-ORD
2h 25mnonstop
$157Southwest
Find Deal
Mon, Mar 3 - Wed, Mar 5
8:20 am - 11:17 amORD-BWI
1h 57mnonstop
7:34 am - 8:56 amBWI-ORD
2h 22mnonstop
$168American Airlines
Find Deal
Wed, Feb 12 - Thu, Feb 13
7:00 am - 9:58 amORD-DCA
1h 58mnonstop
7:25 am - 8:41 amDCA-ORD
2h 16mnonstop
$177United Airlines
Find Deal
Thu, Apr 3 - Mon, Apr 7
1:20 pm - 4:16 pmORD-IAD
1h 56mnonstop
10:20 pm - 11:29 pmIAD-ORD
2h 09mnonstop
$177United Airlines
Find Deal
Mon, Feb 24 - Mon, Feb 24
9:54 am - 3:40 pmMDW-BWI
4h 46m1 stop
6:00 am - 8:45 amBWI-MDW
3h 45m1 stop
$197Delta
Find Deal
Wed, Mar 12 - Thu, Mar 13
6:45 am - 11:41 amORD-BWI
3h 56m1 stop
2:01 pm - 6:47 pmBWI-ORD
5h 46m1 stop
$197Delta
Find Deal
Thu, Feb 13 - Sat, Feb 15
10:26 am - 1:21 pmMDW-BWI
1h 55mnonstop
$28Frontier
Find Deal
Sat, Mar 1
2:36 pm - 5:36 pmMDW-PHL
2h 00mnonstop
$29Frontier
Find Deal
Tue, Apr 1
10:55 am - 1:53 pmORD-BWI
1h 58mnonstop
$69United Airlines
Find Deal
Wed, Mar 5
6:35 pm - 9:20 pmMDW-BWI
1h 45mnonstop
$70Southwest
Find Deal
Tue, Mar 11
4:20 pm - 7:15 pmORD-BWI
1h 55mnonstop
$70Southwest
Find Deal
Sat, Mar 1
6:00 pm - 8:58 pmORD-BWI
1h 58mnonstop
$80American Airlines
Find Deal
Sat, Feb 22
11:10 am - 2:18 pmORD-PHL
2h 08mnonstop
$89United Airlines
Find Deal
Wed, Apr 2
6:42 pm - 11:15 pmMDW-BWI
3h 33m1 stop
$99Delta
Find Deal
Mon, Mar 31
4:58 pm - 11:08 pmORD-BWI
5h 10m1 stop
$99Delta
Find Deal
Fri, Feb 21
6:45 am - 9:46 amORD-PHL
2h 01mnonstop
$100American Airlines
Find Deal
Thu, Apr 24
12:25 pm - 8:50 pmORD-PHL
7h 25m1 stop
6:00 am - 12:29 pmPHL-ORD
7h 29m1 stop
$191Spirit Airlines
Find Deal
Fri, Jan 24 - Fri, Jan 31
4:08 pm - 7:03 pmMDW-BWI
1h 55mnonstop
4:21 pm - 5:33 pmBWI-MDW
2h 12mnonstop
$203Frontier
Find Deal
Mon, Jan 27 - Fri, Feb 28
3:51 pm - 6:43 pmORD-IAD
1h 52mnonstop
10:24 pm - 12:55 pmIAD-ORD
15h 31m1 stop
$377United Airlines
Find Deal
Tue, Jan 28 - Tue, Jan 28
8:20 pm - 9:01 amORD-DCA
11h 41m1 stop
11:59 am - 1:17 pmDCA-ORD
2h 18mnonstop
$377American Airlines
Find Deal
Mon, Jan 27 - Tue, Jan 28
8:05 am - 1:33 pmORD-PHL
4h 28m1 stop
3:55 pm - 5:24 pmPHL-ORD
2h 29mnonstop
$422American Airlines
Find Deal
Sun, Jan 26 - Sun, Jan 26
3:51 pm - 6:43 pmORD-IAD
1h 52mnonstop
10:20 pm - 11:29 pmIAD-ORD
2h 09mnonstop
$468United Airlines
Find Deal
Mon, Jan 27 - Fri, Feb 28
4:55 pm - 12:22 amORD-IAD
6h 27m1 stop
6:59 pm - 11:49 pmIAD-ORD
5h 50m1 stop
$488Delta
Find Deal
Mon, Jan 27 - Fri, Feb 28
4:58 pm - 11:16 pmORD-IAD
5h 18m1 stop
6:00 am - 9:55 amIAD-ORD
4h 55m1 stop
$549Delta
Find Deal
Tue, Jan 28 - Sat, Feb 1
11:25 am - 10:05 pmORD-DCA
9h 40m2 stops
10:55 am - 4:45 pmDCA-ORD
6h 50m1 stop
$587Southwest
Find Deal
Mon, Jan 27 - Tue, Jan 28
9:35 am - 12:25 pmMDW-DCA
1h 50mnonstop
6:05 pm - 7:15 pmDCA-MDW
2h 10mnonstop
$589Southwest
Find Deal
Mon, Jan 27 - Thu, Jan 30
10:26 am - 1:21 pmMDW-BWI
1h 55mnonstop
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
$53Frontier
Find Deal
Sat, Feb 22 - Wed, Feb 26
10:26 am - 1:21 pmMDW-BWI
1h 55mnonstop
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
$54Frontier
Find Deal
Sat, Feb 22 - Wed, Feb 26
12:26 pm - 3:21 pmMDW-BWI
1h 55mnonstop
4:11 pm - 5:23 pmBWI-MDW
2h 12mnonstop
$58Frontier
Find Deal
Wed, Mar 12 - Wed, Mar 19
10:26 am - 1:21 pmMDW-BWI
1h 55mnonstop
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
$59Frontier
Find Deal
Sat, Mar 1 - Wed, Mar 5
7:00 am - 9:55 amORD-BWI
1h 55mnonstop
11:45 am - 1:05 pmBWI-ORD
2h 20mnonstop
$138Southwest
Find Deal
Wed, Mar 5 - Tue, Mar 11
10:55 am - 1:53 pmORD-BWI
1h 58mnonstop
10:50 am - 12:05 pmBWI-ORD
2h 15mnonstop
$139United Airlines
Find Deal
Sat, Mar 1 - Wed, Apr 2
8:15 am - 11:10 amORD-BWI
1h 55mnonstop
6:07 pm - 7:29 pmBWI-ORD
2h 22mnonstop
$149American Airlines
Find Deal
Wed, Mar 5 - Tue, Mar 11
6:20 pm - 9:10 pmMDW-BWI
1h 50mnonstop
8:50 pm - 10:00 pmBWI-MDW
2h 10mnonstop
$158Southwest
Find Deal
Sat, Mar 1 - Mon, Mar 3
6:00 pm - 8:58 pmORD-BWI
1h 58mnonstop
7:34 am - 8:50 amBWI-ORD
2h 16mnonstop
$168American Airlines
Find Deal
Sat, Mar 1 - Tue, Mar 4
12:45 pm - 3:36 pmORD-DCA
1h 51mnonstop
1:00 pm - 2:21 pmDCA-ORD
2h 21mnonstop
$177United Airlines
Find Deal
Thu, Feb 20 - Thu, Feb 27

Spirit Airlines flights from Chicago to Maryland

Our best Spirit Airlines deals on Chicago to Maryland flight tickets
Spirit Airlines
Feb 9
ORD12:25 pmChicago O'Hare Intl
7h 25m
1 stop
PHL8:50 pmPhiladelphia
Feb 11
PHL6:00 amPhiladelphia
7h 29m
1 stop
ORD12:29 pmChicago O'Hare Intl
Spirit Airlines
Mar 24
ORD7:07 pmChicago O'Hare Intl
14h 06m
1 stop
PHL10:13 amPhiladelphia
Mar 31
PHL6:39 pmPhiladelphia
16h 05m
1 stop
ORD9:44 amChicago O'Hare Intl
Spirit Airlines
May 1
ORD6:15 amChicago O'Hare Intl
5h 22m
1 stop
BWI12:37 pmBaltimore/Washington
May 5
BWI2:59 pmBaltimore/Washington
8h 22m
1 stop
ORD10:21 pmChicago O'Hare Intl

JetBlue flights from Chicago to Maryland

Our best JetBlue deals on Chicago to Maryland flight tickets
JetBlue
Feb 19
ORD12:45 pmChicago O'Hare Intl
8h 42m
1 stop
PHL10:27 pmPhiladelphia
Feb 24
PHL6:00 amPhiladelphia
7h 00m
1 stop
ORD12:00 pmChicago O'Hare Intl
JetBlue
Apr 3
ORD1:24 pmChicago O'Hare Intl
6h 35m
1 stop
DCA8:59 pmWashington, D.C. Reagan-National
Apr 8
DCA7:00 amWashington, D.C. Reagan-National
6h 27m
1 stop
ORD12:27 pmChicago O'Hare Intl
JetBlue
Feb 4
ORD7:00 amChicago O'Hare Intl
9h 00m
1 stop
DCA5:00 pmWashington, D.C. Reagan-National
Feb 12
DCA11:45 amWashington, D.C. Reagan-National
7h 10m
1 stop
ORD5:55 pmChicago O'Hare Intl

See travel insights to Maryland from

How to get the cheapest flight ticket from Chicago to Maryland

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Maryland?

The cheapest month to fly to Maryland from Chicago is in August. Flight prices, which tend to average around $203, are often lower during this time because this is during the off-season. If you don’t want to visit Maryland in August, then you should wait until September to fly from Chicago, when ticket prices are also cheap, with an average price of $204.

What is the cheapest day to depart on your flight to Maryland?

The cheapest day to depart from Chicago to Maryland is on a Thursday. Travelers who choose to depart for Maryland on a Thursday will often find tickets for as low as $298. The most expensive day to fly to Maryland is Monday, with ticket prices averaging around $435.

What is the cheapest time of day to depart on your flight to Maryland?

Our most recent data shows that the best time of day to fly to Maryland is in the morning. Flights from Chicago to Maryland during this time can be as low as $307. In contrast, the most expensive time of day to depart to Maryland is at noon when prices are around $518.

What is the cheapest Chicago to Maryland flight route?

Fly from Chicago Midway to Baltimore/Washington for the best Chicago - Maryland flight prices

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

You are more likely to see cheaper flights to Maryland from Chicago when booking 15 weeks ahead of your departure date. In general, you can expect to find flights to Maryland for around $275 when searching 15 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Maryland from Chicago for as low as $164 on momondo.

What cabin class options are available on Chicago to Maryland flights?

There are 4 cabin classes available to choose from on Chicago to Maryland flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap Chicago to Maryland flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Maryland

Best Price Found

$28

Fastest flight time

1h 40m

Direct flights

Every day

Airports in Maryland

4 airports
The best one-way flight to Maryland from Chicago in the past 72 hours is $28. The best round-trip flight deal from Chicago to Maryland found on momondo in the last 72 hours is $53.
The fastest flight from Chicago to Maryland takes 1h 40m
Direct flights go from Chicago to Maryland every day.
There are 4 airports near Maryland: Washington, D.C. Reagan-National (DCA), Baltimore/Washington (BWI), Philadelphia (PHL), Washington, D.C. Dulles Intl (IAD)

  • When did momondo last update prices for flights from Chicago to Maryland?

    Prices for flights from Chicago to Maryland were last updated today.

  • How many operators does momondo search for flights from Chicago to Maryland?

  • How old do you have to be to fly from Chicago to Maryland?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Maryland.

  • What documentation or ID do you need to fly to Maryland?

    The travel and health documents required for your trip to Maryland can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Maryland. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Chicago to Maryland?


Best airlines flying from Chicago to Maryland

Compare and see reviews for airlines that fly from Chicago to Maryland with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $66Free CancellationRating
6.0
3,440 reviews
Search Frontier flights
American AirlinesPriceFrom $119Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Spirit AirlinesPriceFrom $135Free CancellationRating
6.3
8,108 reviews
Search Spirit Airlines flights
SouthwestPriceFrom $138Free CancellationRating
8.1
4,647 reviews
Search Southwest flights
United AirlinesPriceFrom $159Free CancellationRating
7.4
8,970 reviews
Search United Airlines flights
DeltaPriceFrom $176Free CancellationRating
8.0
8,508 reviews
Search Delta flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Maryland?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Maryland for you.

Can I find flights from Chicago to Maryland with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Maryland from Chicago with this policy.

How can momondo help me find flights from Chicago to Maryland?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Maryland from Chicago.

I’m not ready to book a flight from Chicago to Maryland right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Maryland now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Maryland and let you know when they change.


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Popular flights according to clicks in the last 7 days on momondo