$61 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 11/15. 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

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Everything you should know

Cheapest round-trip
$106
Overall average: $230
Multiple Airlines
Fri 10/31Sat 11/15
PHL - ORD • Non-stop
Cheapest non-stop
$107
Typical prices: $123-$264
Frontier
Mon 10/27Thu 10/30
PHL - MDW • Non-stop
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We hope you love your trip to Chicago!
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

Fri, Oct 31 - Sat, Nov 15
Multiple Airlines Logo
6:00 am - 7:26 amPHL-ORD
2h 26mnonstop
Multiple Airlines Logo
3:26 pm - 11:26 pmORD-PHL
7h 00m1 stop
$106Multiple Airlines
Find Deal
Fri, Oct 31 - Mon, Nov 3
Frontier Logo
6:00 am - 7:26 amPHL-ORD
2h 26mnonstop
Frontier Logo
5:15 am - 3:00 pmORD-PHL
8h 45m1 stop
$107Frontier
Find Deal
Fri, Oct 31 - Mon, Nov 3
Frontier Logo
1:19 pm - 2:33 pmPHL-MDW
2h 14mnonstop
Frontier Logo
9:32 am - 11:20 pmMDW-PHL
12h 48m1 stop
$107Frontier
Find Deal
Mon, Nov 17 - Tue, Nov 18
Multiple Airlines Logo
6:00 am - 7:26 amPHL-ORD
2h 26mnonstop
Multiple Airlines Logo
5:10 am - 2:15 pmORD-PHL
8h 05m1 stop
$109Multiple Airlines
Find Deal
Tue, Nov 11 - Tue, Nov 18
Spirit Airlines Logo
9:36 pm - 9:47 amBWI-ORD
13h 11m1 stop
Spirit Airlines Logo
5:10 am - 3:47 pmORD-BWI
9h 37m1 stop
$129Spirit Airlines
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Mon, Nov 10 - Tue, Nov 11
Spirit Airlines Logo
9:36 pm - 9:47 amBWI-ORD
13h 11m1 stop
Spirit Airlines Logo
10:52 am - 11:07 pmORD-BWI
11h 15m1 stop
$130Spirit Airlines
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Wed, Nov 12 - Wed, Nov 19
United Airlines Logo
6:00 am - 7:25 amPHL-ORD
2h 25mnonstop
United Airlines Logo
7:25 am - 10:24 amORD-PHL
1h 59mnonstop
$149United Airlines
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Tue, Nov 11 - Tue, Nov 18
Southwest Logo
4:00 pm - 5:10 pmPHL-MDW
2h 10mnonstop
Southwest Logo
2:25 pm - 5:15 pmMDW-PHL
1h 50mnonstop
$149Southwest
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Sat, Nov 15 - Sun, Nov 16
Southwest Logo
2:20 pm - 3:30 pmPHL-MDW
2h 10mnonstop
Southwest Logo
9:05 am - 12:00 pmMDW-PHL
1h 55mnonstop
$158Southwest
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Wed, Nov 5 - Sat, Nov 8
United Airlines Logo
6:15 am - 7:31 amBWI-ORD
2h 16mnonstop
United Airlines Logo
7:05 am - 9:59 amORD-BWI
1h 54mnonstop
$159United Airlines
Find Deal
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$61
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from Baltimore 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.

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
Munster
Chesterton
Schererville
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 $803
Business Class flights to Chicagofrom $850
Prem Econ Class flights to Chicagofrom $375
Economy Class flights to Chicagofrom $107

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