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$33 Find Cheap Flights from Maryland to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 11/23. 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

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In the last 7 days travelers have searched 46,479,581 times on KAYAK, and here is why:

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Good to know

Low season

January

High season

October

Cheapest flight

$33
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Philadelphia to Chicago O'Hare Airport

FAQs for booking flights from Maryland to Chicago

  • How does KAYAK find such low prices on flights from Maryland to Chicago?

    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 Maryland to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Maryland to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from 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 Maryland to Chicago?

    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 Chicago with an airline and back to Maryland with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Maryland to Chicago?

    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 Chicago from Maryland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Maryland to Chicago?

Find which airlines fly direct from Maryland to Chicago, which days they fly and book direct flights.

Nonstop departures

Maryland to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Tuesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Nonstop returns

Chicago to Maryland

Monday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Tuesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

See more direct flights
See more direct flights

Book cheap flights from Maryland to Chicago

Recent round-trip flight deals

11/20ons
nonstopFrontier
2h 26mPHL-ORD
11/23lör
nonstopFrontier
1h 59mORD-PHL
$62
11/20ons
nonstopFrontier
2h 26mPHL-ORD
11/23lör
nonstopFrontier
1h 59mORD-PHL
$63
11/22fre
nonstopUnited Airlines
2h 13mDCA-ORD
11/24sön
nonstopUnited Airlines
1h 48mORD-DCA
$115
11/22fre
nonstopUnited Airlines
2h 04mIAD-ORD
11/24sön
nonstopUnited Airlines
1h 56mORD-IAD
$115
11/12tis
1 stop
5h 22mBWI-ORD
11/14tors
1 stop
6h 03mORD-BWI
$123
12/6fre
nonstopSouthwest
2h 10mPHL-MDW
12/7lör
nonstopSouthwest
1h 55mMDW-PHL
$127
11/19tis
1 stop
5h 22mBWI-ORD
11/22fre
1 stop
12h 48mORD-BWI
$130
11/18mån
1 stopSpirit Airlines
7h 25mBWI-ORD
11/18mån
1 stopSpirit Airlines
14h 29mORD-BWI
$137
12/7lör
nonstopSouthwest
2h 15mPHL-MDW
12/9mån
nonstopSouthwest
1h 50mMDW-PHL
$139
11/18mån
1 stopSpirit Airlines
7h 25mBWI-ORD
11/19tis
2 stopsSpirit Airlines
20h 02mORD-BWI
$153

Search by stops

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Recent one-way flight deals

11/23lör
nonstopFrontier
2h 26mPHL-ORD
$33
2/12ons
nonstopFrontier
2h 13mPHL-MDW
$33
11/25mån
nonstopUnited Airlines
2h 13mDCA-ORD
$58
11/25mån
nonstopUnited Airlines
2h 04mIAD-ORD
$58
12/5tors
nonstopAmerican Airlines
2h 28mPHL-ORD
$58
12/4ons
nonstopSouthwest
2h 10mPHL-MDW
$58
12/10tis
nonstopSouthwest
2h 05mBWI-MDW
$58
12/17tis
nonstopAmerican Airlines
2h 29mPHL-ORD
$59
12/4ons
2 stopsSpirit Airlines
14h 20mBWI-ORD
$71
12/3tis
1 stopSpirit Airlines
6h 01mBWI-ORD
$73

Search by stops

Search by airline

Search by price

Last minute flights from Maryland to Chicago

Last minute flight, train and bus deals

11/4mån
nonstopFrontier
2h 19mPHL-ORD
11/7tors
nonstopFrontier
1h 59mORD-PHL
$91
11/4mån
nonstopFrontier
2h 17mPHL-MDW
11/7tors
nonstopFrontier
2h 01mMDW-PHL
$91
11/4mån
nonstop
2h 19mPHL-ORD
11/6ons
multi-stop
12h 31mORD-PHL
$162
11/2lör
multi-stop
10h 23mPHL-ORD
11/3sön
nonstop
2h 03mORD-PHL
$185
11/4mån
multi-stopSpirit Airlines
15h 58mPHL-ORD
11/6ons
multi-stopSpirit Airlines
12h 31mORD-PHL
$223
11/2lör
multi-stopSpirit Airlines
10h 23mPHL-ORD
11/5tis
multi-stopSpirit Airlines
21h 57mORD-PHL
$238
11/5tis
multi-stopSouthwest
7h 25mIAD-MDW
11/7tors
multi-stopSouthwest
8h 45mMDW-IAD
$301
11/5tis
nonstopSouthwest
2h 10mPHL-MDW
11/6ons
nonstopSouthwest
1h 50mMDW-PHL
$340
11/5tis
nonstopUnited Airlines
2h 13mDCA-ORD
11/5tis
nonstopUnited Airlines
1h 48mORD-DCA
$357
11/5tis
multi-stopUnited Airlines
5h 44mDCA-ORD
11/5tis
nonstopUnited Airlines
2h 03mORD-DCA
$367

Search by stops

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Everything you need to know for your flight to Chicago

Cabin class types available on flights to Maryland

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