$99 Find Cheap Flights from Maryland to Chicago - Compare and Save

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 7/28. 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, Oct 22 - Sun, Oct 25
Frontier Logo
4:47 pm - 6:24 pm
PHL
-
ORD
2h 37mnonstop
Frontier Logo
9:33 pm - 7:36 am
ORD
-
PHL
9h 03m
1 stop
$223Frontier
Fri, Aug 7 - Mon, Aug 17
Frontier Logo
6:11 pm - 7:53 pm
PHL
-
ORD
2h 42mnonstop
Frontier Logo
8:58 pm - 12:21 am
ORD
-
PHL
2h 23mnonstop
$224Frontier
Mon, Aug 17 - Sat, Aug 22
Southwest Logo
5:55 am - 12:15 pm
PHL
-
MDW
7h 20m
2 stops
Southwest Logo
8:05 am - 4:10 pm
MDW
-
PHL
7h 05m
1 stop
$227Southwest
Wed, Jul 29 - Thu, Aug 6
Multiple Airlines Logo
4:30 pm - 10:37 am
PHL
-
RFD
19h 07m
2 stops
Multiple Airlines Logo
11:37 am - 12:43 am
RFD
-
PHL
12h 06m
1 stop
$227Multiple Airlines
Thu, Sep 10 - Mon, Sep 14
Southwest Logo
6:05 pm - 7:10 pm
PHL
-
MDW
2h 05mnonstop
Southwest Logo
7:25 am - 3:25 pm
MDW
-
PHL
7h 00m
1 stop
$228Southwest
Fri, Oct 2 - Mon, Oct 5
Delta Logo
3:54 pm - 10:45 pm
PHL
-
MDW
7h 51m
1 stop
Delta Logo
5:11 pm - 12:41 am
MDW
-
PHL
6h 30m
1 stop
$229Delta
Mon, Aug 17 - Thu, Aug 20
Multiple Airlines Logo
6:33 pm - 12:50 pm
PHL
-
ORD
19h 17m
2 stops
Multiple Airlines Logo
6:00 am - 9:17 am
ORD
-
PHL
2h 17mnonstop
$231Multiple Airlines
Thu, Aug 6 - Mon, Aug 10
Delta Logo
12:30 pm - 4:17 pm
BWI
-
ORD
4h 47m
1 stop
Delta Logo
6:40 am - 1:05 pm
ORD
-
BWI
5h 25m
1 stop
$236Delta
Sat, Aug 8 - Mon, Aug 10
American Airlines Logo
8:10 pm - 9:37 pm
BWI
-
ORD
2h 27mnonstop
American Airlines Logo
5:49 pm - 10:58 pm
ORD
-
BWI
4h 09m
1 stop
$238American Airlines
Thu, Aug 20 - Mon, Aug 24
American Airlines Logo
10:18 am - 11:38 am
DCA
-
ORD
2h 20mnonstop
American Airlines Logo
10:53 am - 1:54 pm
ORD
-
DCA
2h 01mnonstop
$246American Airlines
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Good to know

Low seasonFebruary
Cheapest flight$99
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 12% increase in price.
Flight from Reagan Washington National Airport 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
Munster
Chesterton
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 $439
Business Class flights to Chicagofrom $401
Premium Economy Class flights to Chicagofrom $375
Economy Class flights to Chicagofrom $220