$55 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 2/26. 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

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Everything you should know

Cheapest round-trip
$103
Overall average: $299
Frontier
Thu 1/8Mon 1/12
PHL - ORD • 1 stop
Cheapest non-stop
$103
Typical prices: $113-$325
Frontier
Mon 11/24Sat 11/29
PHL - MDW • Non-stop
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Flight Deals
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Flight Deals

Cheap Flights from Maryland to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Maryland to Chicago 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 Maryland to Chicago

Thu, Jan 8 - Mon, Jan 12
Frontier Logo
12:03 pm - 10:53 amPHL-ORD
23h 50m1 stop
Frontier Logo
3:32 pm - 6:47 pmORD-PHL
2h 15mnonstop
$103Frontier
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Mon, Nov 24 - Sat, Nov 29
Frontier Logo
4:50 pm - 6:06 pmPHL-MDW
2h 16mnonstop
Frontier Logo
8:29 pm - 11:26 pmMDW-PHL
1h 57mnonstop
$103Frontier
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Fri, Dec 5 - Sun, Dec 7
Frontier Logo
11:10 am - 12:40 pmPHL-ORD
2h 30mnonstop
Frontier Logo
7:00 am - 5:31 amORD-PHL
21h 31m1 stop
$104Frontier
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Mon, Nov 24 - Mon, Nov 24
Frontier Logo
4:50 pm - 6:06 pmPHL-MDW
2h 16mnonstop
Frontier Logo
7:10 pm - 10:06 pmMDW-PHL
1h 56mnonstop
$104Frontier
Find Deal
Wed, Dec 31 - Wed, Jan 7
Multiple Airlines Logo
6:36 pm - 8:06 pmPHL-ORD
2h 30mnonstop
Multiple Airlines Logo
6:05 pm - 1:14 amORD-PHL
30h 09m1 stop
$106Multiple Airlines
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Fri, Dec 5 - Sun, Dec 7
Multiple Airlines Logo
10:40 am - 9:48 pmBWI-ORD
12h 08m1 stop
Multiple Airlines Logo
5:11 am - 8:18 amORD-BWI
2h 07mnonstop
$116Multiple Airlines
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Fri, Mar 6 - Tue, Mar 10
JetBlue Logo
6:00 am - 11:49 amDCA-ORD
6h 49m1 stop
JetBlue Logo
10:00 am - 6:55 pmORD-DCA
7h 55m1 stop
$186JetBlue
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Fri, Nov 28 - Sun, Nov 30
JetBlue Logo
1:55 pm - 7:55 pmDCA-ORD
7h 00m1 stop
JetBlue Logo
8:04 am - 2:59 pmORD-DCA
5h 55m1 stop
$196JetBlue
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Wed, Dec 3 - Tue, Dec 9
Southwest Logo
9:30 am - 10:35 amDCA-MDW
2h 05mnonstop
Southwest Logo
12:15 pm - 3:00 pmMDW-DCA
1h 45mnonstop
$231Southwest
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Tue, Feb 17 - Fri, Feb 20
Southwest Logo
9:00 pm - 10:15 pmDCA-MDW
2h 15mnonstop
Southwest Logo
4:35 pm - 7:25 pmMDW-DCA
1h 50mnonstop
$234Southwest
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Useful Info

Good to know

Low seasonJanuary
Cheapest flight$55
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Baltimore to Chicago Midway 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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Saint John
Griffith

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.
First Class flights to Chicagofrom $717
Business Class flights to Chicagofrom $361
Prem Econ Class flights to Chicagofrom $375
Economy Class flights to Chicagofrom $96