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.

$89 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

Thu, Nov 5 - Sun, Nov 8

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

$167Frontier

Sun, Sep 6 - Sun, Sep 6

10:22 am - 11:55 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 33mnonstop

8:30 pm - 11:53 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 23mnonstop

$168Frontier

Sat, Jan 23 - Wed, Jan 27

11:40 am - 12:59 pmBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 19mnonstop

9:12 pm - 12:16 amORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 04mnonstop

$177American Airlines

Sat, Nov 14 - Mon, Nov 16

7:16 am - 8:50 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 34mnonstop

9:00 pm - 11:59 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

1h 59mnonstop

$177American Airlines

Mon, Oct 5 - Mon, Oct 5

6:25 am - 7:46 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 21mnonstop

2:30 pm - 5:43 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 13mnonstop

$177United Airlines

Mon, Oct 12 - Wed, Oct 14

9:09 am - 10:29 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 20mnonstop

5:55 pm - 9:02 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 07mnonstop

$177United Airlines

Thu, Sep 10 - Sat, Sep 12

6:30 am - 7:30 amBWI Baltimore/Washington-MDW Chicago Midway

2h 00mnonstop

5:55 am - 8:40 amMDW Chicago Midway-BWI Baltimore/Washington

1h 45mnonstop

$177Southwest

Sat, Sep 26 - Mon, Sep 28

3:45 pm - 4:45 pmBWI Baltimore/Washington-MDW Chicago Midway

2h 00mnonstop

9:00 am - 11:55 amMDW Chicago Midway-BWI Baltimore/Washington

1h 55mnonstop

$177Southwest

Tue, Sep 29 - Sat, Oct 3

6:10 am - 9:07 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

3h 57m1 stop Detroit Metropolitan Wayne County

4:30 pm - 11:44 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

6h 14m1 stop Atlanta Hartsfield-Jackson

$184Delta

Thu, Oct 22 - Mon, Oct 26

6:05 am - 9:17 amIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

4h 12m1 stop Detroit Metropolitan Wayne County

9:29 am - 4:28 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

5h 59m1 stop Detroit Metropolitan Wayne County

$197Delta

Recent last minute flight deals from Maryland to Chicago

Fri, Aug 28 - Mon, Sep 28

6:37 pm - 8:05 pmBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 28mnonstop

6:20 am - 9:25 amORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 05mnonstop

$185Frontier

Fri, Aug 28 - Mon, Sep 28

1:24 pm - 3:59 pmBWI Baltimore/Washington-ORD Chicago O'Hare Intl

27h 35m1 stop Houston George Bush Intcntl

6:20 am - 9:25 amORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 05mnonstop

$203Frontier

Tue, Aug 25 - Fri, Sep 25

5:16 pm - 11:08 pmPHL Philadelphia-ORD Chicago O'Hare Intl

6h 52m1 stop Orlando

3:00 pm - 11:07 pmORD Chicago O'Hare Intl-PHL Philadelphia

7h 07m1 stop Fort Lauderdale

$309Multiple Airlines

Fri, Aug 28 - Mon, Sep 28

8:00 pm - 9:00 pmBWI Baltimore/Washington-MDW Chicago Midway

2h 00mnonstop

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

1h 55mnonstop

$315Southwest

Fri, Aug 28 - Mon, Sep 28

4:55 pm - 7:50 pmBWI Baltimore/Washington-MDW Chicago Midway

3h 55m1 stop Norfolk

9:00 am - 11:55 amMDW Chicago Midway-BWI Baltimore/Washington

1h 55mnonstop

$321Southwest

Fri, Aug 28 - Mon, Sep 28

5:23 pm - 6:54 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 31mnonstop

5:00 pm - 8:06 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 06mnonstop

$325American Airlines

Fri, Aug 28 - Mon, Sep 28

8:32 am - 12:15 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

4h 43m1 stop Charlotte Douglas

10:35 am - 1:38 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 03mnonstop

$335American Airlines

Tue, Aug 25 - Fri, Sep 25

6:56 pm - 8:26 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 30mnonstop

4:00 pm - 7:24 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 24mnonstop

$365United Airlines

Sat, Aug 29 - Sat, Sep 5

10:34 am - 11:59 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 25mnonstop

9:05 am - 12:23 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 18mnonstop

$368United Airlines

Thu, Aug 27 - Sun, Oct 18

2:45 pm - 7:59 pmPHL Philadelphia-ORD Chicago O'Hare Intl

6h 14m1 stop Atlanta Hartsfield-Jackson

6:20 am - 2:30 pmORD Chicago O'Hare Intl-PHL Philadelphia

31h 10m2 stops New York John F Kennedy Intl Boston Logan Intl

$437Multiple Airlines

Recent direct flight deals from Maryland to Chicago

Thu, Nov 5 - Sun, Nov 8

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

$167Frontier

Sun, Sep 6 - Sun, Sep 6

10:22 am - 11:55 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 33mnonstop

8:30 pm - 11:53 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 23mnonstop

$168Frontier

Mon, Sep 14 - Fri, Sep 18

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

Sat, Jan 23 - Wed, Jan 27

11:40 am - 12:59 pmBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 19mnonstop

9:12 pm - 12:16 amORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 04mnonstop

$177American Airlines

Thu, Oct 8 - Tue, Oct 13

7:17 am - 8:45 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 28mnonstop

9:12 pm - 12:16 amORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 04mnonstop

$177American Airlines

Mon, Oct 5 - Mon, Oct 5

6:25 am - 7:46 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 21mnonstop

2:30 pm - 5:43 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 13mnonstop

$177United Airlines

Mon, Oct 12 - Wed, Oct 14

9:09 am - 10:29 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 20mnonstop

5:55 pm - 9:02 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 07mnonstop

$177United Airlines

Thu, Oct 15 - Mon, Oct 19

9:00 am - 10:00 amBWI Baltimore/Washington-MDW Chicago Midway

2h 00mnonstop

8:55 pm - 11:45 pmMDW Chicago Midway-BWI Baltimore/Washington

1h 50mnonstop

$177Southwest

Thu, Sep 10 - Sat, Sep 12

6:30 am - 7:30 amBWI Baltimore/Washington-MDW Chicago Midway

2h 00mnonstop

5:55 am - 8:40 amMDW Chicago Midway-BWI Baltimore/Washington

1h 45mnonstop

$177Southwest

Sat, Nov 14 - Mon, Nov 16

7:16 am - 8:50 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 34mnonstop

9:00 pm - 11:59 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

1h 59mnonstop

$177American Airlines

Useful Info

Low season	February
High season	October
Cheapest flight	$89

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

Most popular time to fly and prices are also 17% lower on average.

Flight from Reagan Washington National Airport 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

Saint Joseph

Hammond

Portage

Lansing

Valparaiso

Munster

Schererville

Chesterton

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

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Return flight deals

Cabin class types available on flights to Maryland

First Class flights to Chicagofrom $437

Business Class flights to Chicagofrom $437

Premium Economy Class flights to Chicagofrom $375

Economy Class flights to Chicagofrom $126

$89 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

Good to know

Low season

High season

Cheapest flight

FAQs for booking flights from Maryland to Chicago

Traveling to a place near Chicago?

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Maryland

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

Find direct flights for Chicago

Flights to other popular destinations

Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Find deals for your return flight