$94 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 7/21. 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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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, Jun 26 - Mon, Jun 29
Frontier Logo
5:06 pm - 6:47 pm
PHL
-
ORD
2h 41mnonstop
Frontier Logo
8:00 pm - 11:32 pm
ORD
-
PHL
2h 32mnonstop
$191Frontier
Tue, Jul 7 - Mon, Jul 13
Frontier Logo
6:00 am - 12:25 pm
PHL
-
ORD
7h 25m
1 stop
Frontier Logo
8:05 pm - 11:31 pm
ORD
-
PHL
2h 26mnonstop
$192Frontier
Wed, Jun 10 - Wed, Jun 17
Southwest Logo
5:20 pm - 8:10 pm
BWI
-
MDW
3h 50m
1 stop
Southwest Logo
8:10 am - 11:10 am
MDW
-
BWI
2h 00mnonstop
$226Southwest
Wed, Jun 17 - Tue, Jun 23
Southwest Logo
8:30 pm - 9:35 pm
BWI
-
MDW
2h 05mnonstop
Southwest Logo
12:50 pm - 5:55 pm
MDW
-
BWI
4h 05m
1 stop
$230Southwest
Tue, Jun 16 - Tue, Jun 23
American Airlines Logo
10:06 am - 3:48 pm
BWI
-
ORD
6h 42m
1 stop
American Airlines Logo
9:00 pm - 11:59 pm
ORD
-
BWI
1h 59mnonstop
$230American Airlines
Wed, Jul 1 - Tue, Jul 7
American Airlines Logo
7:29 am - 11:00 am
DCA
-
ORD
4h 31m
1 stop
American Airlines Logo
9:42 am - 12:44 pm
ORD
-
DCA
2h 02mnonstop
$233American Airlines
Sat, Sep 26 - Wed, Sep 30
United Airlines Logo
10:45 am - 11:47 am
BWI
-
ORD
2h 02mnonstop
United Airlines Logo
9:30 pm - 12:38 am
ORD
-
BWI
2h 08mnonstop
$233United Airlines
Thu, Jun 4 - Wed, Jun 10
United Airlines Logo
8:15 am - 9:36 am
IAD
-
ORD
2h 21mnonstop
United Airlines Logo
6:30 am - 9:24 am
ORD
-
IAD
1h 54mnonstop
$237United Airlines
Wed, Aug 26 - Sat, Aug 29
Delta Logo
1:30 pm - 6:03 pm
DCA
-
ORD
5h 33m
1 stop
Delta Logo
6:40 am - 12:42 pm
ORD
-
DCA
5h 02m
1 stop
$238Delta
Sat, Jun 6 - Wed, Jun 10
Delta Logo
6:00 am - 8:43 am
IAD
-
MDW
3h 43m
1 stop
Delta Logo
6:00 am - 11:39 am
MDW
-
IAD
4h 39m
1 stop
$238Delta
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$94
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 4% 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.

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
Schererville
Chesterton
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.