$82 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 4/23. 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
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

Thu, Apr 23 - Mon, Apr 27
Frontier Logo
10:00 pm - 5:54 pm
BWI
-
MDW
20h 54m
1 stop
Frontier Logo
2:15 pm - 12:44 am
MDW
-
BWI
9h 29m
1 stop
$173Frontier
Tue, Apr 14 - Fri, Apr 17
Multiple Airlines Logo
12:17 pm - 5:00 pm
BWI
-
ORD
5h 43m
1 stop
Multiple Airlines Logo
7:15 pm - 9:15 am
ORD
-
BWI
13h 00m
1 stop
$173Multiple Airlines
Wed, Apr 15 - Sun, Apr 19
Multiple Airlines Logo
12:17 pm - 5:00 pm
BWI
-
ORD
5h 43m
1 stop
Multiple Airlines Logo
7:15 pm - 9:15 am
ORD
-
BWI
13h 00m
1 stop
$174Multiple Airlines
Sat, Apr 18 - Mon, Apr 20
Multiple Airlines Logo
11:46 am - 9:12 pm
BWI
-
ORD
10h 26m
2 stops
Multiple Airlines Logo
11:28 am - 11:22 am
ORD
-
BWI
22h 54m
1 stop
$175Multiple Airlines
Mon, Apr 20 - Thu, Apr 23
Frontier Logo
4:10 pm - 5:36 pm
BWI
-
ORD
2h 26mnonstop
Frontier Logo
2:05 pm - 4:40 pm
ORD
-
BWI
25h 35m
1 stop
$176Frontier
Thu, Apr 16 - Mon, Apr 20
Multiple Airlines Logo
2:30 pm - 7:59 am
BWI
-
MDW
18h 29m
1 stop
Multiple Airlines Logo
2:15 pm - 11:22 am
MDW
-
BWI
20h 07m
1 stop
$177Multiple Airlines
Wed, Jun 3 - Thu, Jun 4
Southwest Logo
9:05 am - 3:45 pm
DCA
-
MDW
7h 40m
2 stops
Southwest Logo
11:15 am - 2:00 pm
MDW
-
DCA
1h 45mnonstop
$223Southwest
Sat, May 16 - Wed, May 20
Southwest Logo
8:45 am - 5:00 pm
DCA
-
MDW
9h 15m
1 stop
Southwest Logo
8:15 am - 11:05 am
MDW
-
DCA
1h 50mnonstop
$224Southwest
Wed, Apr 22 - Mon, Apr 27
Delta Logo
1:50 pm - 6:39 pm
DCA
-
ORD
5h 49m
1 stop
Delta Logo
1:36 pm - 6:59 pm
ORD
-
DCA
4h 23m
1 stop
$228Delta
Wed, Apr 22 - Mon, Apr 27
Delta Logo
7:19 pm - 11:59 pm
IAD
-
ORD
5h 40m
1 stop
Delta Logo
5:04 pm - 11:03 pm
ORD
-
IAD
4h 59m
1 stop
$228Delta
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$82
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 1% 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
Chesterton
Schererville
Munster
Porter
Monticello
Griffith
Saint John

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 $354
Business Class flights to Chicagofrom $821
Premium Economy Class flights to Chicagofrom $375
Economy Class flights to Chicagofrom $177