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.

$92 CHEAP FLIGHTS from Maryland to Chicago

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Cheap Flights from Maryland to Chicago

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Maryland to Chicago

Mon, Oct 19 - Thu, Oct 22

9:09 pm - 10:39 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 30mnonstop

10:26 am - 6:15 pmORD Chicago O'Hare Intl-PHL Philadelphia

6h 49m1 stop Atlanta Hartsfield-Jackson

$166Frontier

Mon, Nov 2 - Thu, Nov 5

8:30 am - 6:45 pmPHL Philadelphia-ORD Chicago O'Hare Intl

11h 15m1 stop Atlanta Hartsfield-Jackson

4:42 pm - 7:58 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 16mnonstop

$167Frontier

Wed, Oct 28 - Thu, Oct 29

5:27 pm - 11:00 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

6h 33m1 stop Charlotte Douglas

3:16 pm - 9:44 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

5h 28m1 stop Columbus

$180American Airlines

Tue, Sep 22 - Wed, Sep 23

6:05 am - 7:26 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 21mnonstop

10:49 am - 1:58 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 09mnonstop

$192United Airlines

Sat, Oct 31 - Sat, Oct 31

6:10 am - 7:29 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 19mnonstop

11:00 am - 2:06 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 06mnonstop

$206United Airlines

Wed, Oct 28 - Thu, Oct 29

5:48 pm - 11:00 pmBWI Baltimore/Washington-ORD Chicago O'Hare Intl

6h 12m1 stop Charlotte Douglas

7:59 am - 11:01 amORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 02mnonstop

$227American Airlines

Wed, Oct 21 - Sun, Oct 25

1:56 pm - 8:50 amBWI Baltimore/Washington-RFD Chicago Greater Rockford

19h 54m1 stop Fort Lauderdale

10:20 am - 1:01 pmRFD Chicago Greater Rockford-BWI Baltimore/Washington

25h 41m1 stop Fort Lauderdale

$237Multiple Airlines

Mon, Oct 5 - Wed, Oct 7

11:54 am - 1:30 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

7:11 am - 11:18 pmORD Chicago O'Hare Intl-PHL Philadelphia

15h 07m3 stops Fort Lauderdale Tampa Atlanta Hartsfield-Jackson

$238Multiple Airlines

Thu, Oct 22 - Sat, Oct 24

1:55 pm - 3:00 pmPHL Philadelphia-MDW Chicago Midway

2h 05mnonstop

8:00 am - 11:00 amMDW Chicago Midway-PHL Philadelphia

2h 00mnonstop

$277Southwest

Mon, Sep 28 - Mon, Oct 5

12:45 pm - 1:45 pmPHL Philadelphia-MDW Chicago Midway

2h 00mnonstop

6:55 pm - 9:55 pmMDW Chicago Midway-PHL Philadelphia

2h 00mnonstop

$277Southwest

Recent last minute flight deals from Maryland to Chicago

Thu, Sep 10 - Wed, Sep 16

11:54 am - 1:30 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

3:50 pm - 11:40 amORD Chicago O'Hare Intl-PHL Philadelphia

18h 50m1 stop Orlando

$175Frontier

Thu, Sep 10 - Wed, Sep 16

11:54 am - 1:30 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

3:50 pm - 12:09 amORD Chicago O'Hare Intl-PHL Philadelphia

7h 19m1 stop Orlando

$185Frontier

Wed, Sep 9 - Sat, Sep 12

11:23 am - 12:40 pmBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 17mnonstop

6:58 am - 10:07 amORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 09mnonstop

$311American Airlines

Thu, Sep 10 - Thu, Sep 10

12:10 pm - 1:31 pmBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 21mnonstop

7:45 pm - 10:59 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 14mnonstop

$311United Airlines

Thu, Sep 10 - Thu, Sep 10

6:05 am - 7:26 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 21mnonstop

7:45 pm - 10:59 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 14mnonstop

$311United Airlines

Thu, Sep 10 - Sat, Sep 12

5:20 pm - 6:15 pmBWI Baltimore/Washington-MDW Chicago Midway

1h 55mnonstop

9:05 am - 12:00 pmMDW Chicago Midway-BWI Baltimore/Washington

1h 55mnonstop

$311Southwest

Thu, Sep 10 - Fri, Sep 11

1:10 pm - 2:05 pmBWI Baltimore/Washington-MDW Chicago Midway

1h 55mnonstop

7:55 pm - 10:50 pmMDW Chicago Midway-BWI Baltimore/Washington

1h 55mnonstop

$311Southwest

Thu, Sep 10 - Sat, Sep 12

2:32 pm - 4:10 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 38mnonstop

8:45 am - 11:52 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 07mnonstop

$317American Airlines

Thu, Sep 10 - Wed, Sep 16

11:54 am - 1:30 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

8:24 pm - 5:48 pmORD Chicago O'Hare Intl-PHL Philadelphia

20h 24m1 stop Boston Logan Intl

$328Multiple Airlines

Thu, Sep 10 - Mon, Sep 21

6:00 pm - 12:23 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

7h 23m1 stop Denver Intl

8:24 pm - 9:42 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

12h 18m1 stop Boston Logan Intl

$339Multiple Airlines

Recent direct flight deals from Maryland to Chicago

Fri, Sep 25 - Mon, Sep 28

11:54 am - 1:30 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

7:25 am - 10:49 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 24mnonstop

$168Frontier

Fri, Oct 30 - Sun, Nov 1

9:09 pm - 10:43 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 34mnonstop

4:42 pm - 7:58 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 16mnonstop

$172Frontier

Fri, Oct 16 - Fri, Oct 23

9:09 pm - 10:39 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 30mnonstop

4:41 pm - 8:04 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 23mnonstop

$172Frontier

Tue, Sep 22 - Wed, Sep 23

6:05 am - 7:26 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 21mnonstop

10:49 am - 1:58 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 09mnonstop

$192United Airlines

Sat, Oct 31 - Sat, Oct 31

6:10 am - 7:29 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 19mnonstop

11:00 am - 2:06 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 06mnonstop

$206United Airlines

Mon, Sep 14 - Wed, Sep 16

8:25 am - 9:45 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 20mnonstop

7:30 am - 10:30 amORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 00mnonstop

$226United Airlines

Mon, Sep 28 - Mon, Oct 5

12:45 pm - 1:45 pmPHL Philadelphia-MDW Chicago Midway

2h 00mnonstop

6:55 pm - 9:55 pmMDW Chicago Midway-PHL Philadelphia

2h 00mnonstop

$277Southwest

Thu, Oct 22 - Sat, Oct 24

1:55 pm - 3:00 pmPHL Philadelphia-MDW Chicago Midway

2h 05mnonstop

8:00 am - 11:00 amMDW Chicago Midway-PHL Philadelphia

2h 00mnonstop

$277Southwest

Wed, Oct 21 - Tue, Oct 27

9:21 am - 11:05 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 44mnonstop

7:37 pm - 10:52 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 15mnonstop

$277American Airlines

Thu, Oct 29 - Thu, Oct 29

5:43 am - 7:25 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 42mnonstop

5:29 pm - 9:07 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 38mnonstop

$277American Airlines

Useful Info

Low season	February
High season	October
Cheapest flight	$92

Best time to beat the crowds with an average 20% drop in price.

Most popular time to fly and prices are also 16% lower on average.

Flight from Philadelphia to Chicago O'Hare Airport

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.

Merrillville

Hammond

Saint Joseph

Portage

Lansing

Valparaiso

Munster

Schererville

Chesterton

Porter

Monticello

Saint John

Griffith

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$92 Find Cheap Flights from Maryland to Chicago - Compare and Save

Cheap Flights from Maryland to Chicago

Recent round-trip flight deals from Maryland to Chicago

Recent one-way flight deals from Maryland to Chicago

Recent last minute flight deals from Maryland to Chicago

Recent direct flight deals from Maryland to Chicago

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High season

Cheapest flight

FAQs for booking flights from Maryland to Chicago

Traveling to a place near Chicago?

More options for your flight to Chicago

Complete your trip to Chicago with a hotel stay or car rental

Cabin class types available on flights to Maryland

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Choose which airport to fly into in Chicago

Flights to other popular destinations

Find deals for your return flight