$89 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 8/15. 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, 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

Sat, Aug 8 - Thu, Aug 27
Frontier Logo
6:05 pm - 7:47 pm
PHL
-
ORD
2h 42mnonstop
Frontier Logo
6:00 am - 9:17 am
ORD
-
PHL
2h 17mnonstop
$187Frontier
Thu, Aug 13 - Mon, Aug 17
Frontier Logo
6:05 pm - 7:47 pm
PHL
-
ORD
2h 42mnonstop
Frontier Logo
8:58 pm - 12:21 am
ORD
-
PHL
2h 23mnonstop
$188Frontier
Mon, Aug 17 - Wed, Aug 19
Multiple Airlines Logo
6:11 pm - 7:53 pm
PHL
-
ORD
2h 42mnonstop
Multiple Airlines Logo
11:01 am - 8:01 pm
ORD
-
PHL
8h 00m
1 stop
$196Multiple Airlines
Thu, Sep 3 - Sun, Sep 6
Southwest Logo
6:30 am - 7:30 am
BWI
-
MDW
2h 00mnonstop
Southwest Logo
7:45 am - 10:40 am
MDW
-
BWI
1h 55mnonstop
$206Southwest
Sat, Aug 15 - Wed, Aug 19
Southwest Logo
6:35 am - 7:35 am
BWI
-
MDW
2h 00mnonstop
Southwest Logo
12:35 pm - 4:40 pm
MDW
-
BWI
3h 05m
1 stop
$207Southwest
Thu, Aug 13 - Sat, Aug 15
Delta Logo
12:03 pm - 4:51 pm
BWI
-
ORD
5h 48m
1 stop
Delta Logo
2:30 pm - 9:28 pm
ORD
-
BWI
5h 58m
1 stop
$207Delta
Sat, Oct 3 - Thu, Oct 8
Multiple Airlines Logo
5:28 pm - 9:18 am
PHL
-
RFD
16h 50m
2 stops
Multiple Airlines Logo
9:40 am - 11:43 pm
RFD
-
PHL
13h 03m
1 stop
$209Multiple Airlines
Sat, Sep 5 - Sat, Sep 12
American Airlines Logo
8:10 pm - 9:37 pm
BWI
-
ORD
2h 27mnonstop
American Airlines Logo
9:40 am - 12:49 pm
ORD
-
BWI
2h 09mnonstop
$214American Airlines
Sat, Sep 5 - Tue, Sep 8
American Airlines Logo
8:09 pm - 9:41 pm
DCA
-
ORD
2h 32mnonstop
American Airlines Logo
6:45 am - 12:19 pm
ORD
-
DCA
4h 34m
1 stop
$221American Airlines
Fri, Sep 11 - Mon, Sep 14
Delta Logo
5:05 pm - 9:37 pm
DCA
-
ORD
5h 32m
1 stop
Delta Logo
5:10 pm - 11:02 pm
ORD
-
DCA
4h 52m
1 stop
$231Delta
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Good to know

Low season

February

Cheapest flight

$89
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly and prices are also 19% lower on average.
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
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 $558
Business Class flights to Chicagofrom $401
Premium Economy Class flights to Chicagofrom $375
Economy Class flights to Chicagofrom $181