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 - Tue, Nov 10

11:05 am - 12:41 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

6:30 am - 1:12 pmORD Chicago O'Hare Intl-PHL Philadelphia

5h 42m1 stop Atlanta Hartsfield-Jackson

$166Frontier

Thu, Oct 29 - Fri, Oct 30

11:05 am - 12:41 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

6:00 am - 2:25 pmORD Chicago O'Hare Intl-PHL Philadelphia

7h 25m1 stop Dallas/Fort Worth

$166Frontier

Mon, Nov 16 - Wed, Nov 18

2:40 pm - 5:45 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

4h 05m1 stop Lambert-St Louis

12:05 pm - 2:55 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$183Southwest

Mon, Dec 7 - Thu, Dec 10

2:40 pm - 5:45 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

4h 05m1 stop Lambert-St Louis

7:25 am - 10:15 amMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$183Southwest

Thu, Oct 8 - Mon, Oct 12

6:10 am - 7:25 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 15mnonstop

9:52 pm - 12:58 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 06mnonstop

$191United Airlines

Tue, Oct 6 - Mon, Oct 12

7:05 pm - 8:24 pmBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 19mnonstop

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

2h 00mnonstop

$192United Airlines

Tue, Sep 15 - Sat, Sep 26

9:04 pm - 11:51 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

15h 47m1 stop Atlanta Hartsfield-Jackson

7:11 am - 6:33 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

10h 22m2 stops Fort Lauderdale Tampa

$194Multiple Airlines

Mon, Aug 31 - Thu, Sep 3

6:40 pm - 12:50 pmPHL Philadelphia-ORD Chicago O'Hare Intl

43h 10m2 stops Tampa Fort Lauderdale

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

2h 23mnonstop

$196Multiple Airlines

Thu, Jan 28 - Wed, Feb 3

6:10 pm - 11:50 pmBWI Baltimore/Washington-ORD Chicago O'Hare Intl

6h 40m1 stop Atlanta Hartsfield-Jackson

5:30 am - 11:48 amORD Chicago O'Hare Intl-BWI Baltimore/Washington

5h 18m1 stop Atlanta Hartsfield-Jackson

$197Delta

Thu, Dec 3 - Sat, Dec 5

8:10 am - 2:38 pmBWI Baltimore/Washington-ORD Chicago O'Hare Intl

7h 28m1 stop Atlanta Hartsfield-Jackson

11:29 am - 4:49 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

4h 20m1 stop Detroit Metropolitan Wayne County

$197Delta

Recent last minute flight deals from Maryland to Chicago

Fri, Aug 21 - Sat, Oct 24

6:00 am - 7:29 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 29mnonstop

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

2h 23mnonstop

$172Frontier

Thu, Aug 20 - Thu, Sep 3

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

2h 33mnonstop

5:55 am - 9:04 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 09mnonstop

$189Frontier

Mon, Aug 24 - Tue, Sep 22

7:03 am - 8:30 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 27mnonstop

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

2h 09mnonstop

$315American Airlines

Sun, Aug 23 - Wed, Sep 23

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

6h 52m1 stop Orlando

7:11 am - 7:04 pmORD Chicago O'Hare Intl-PHL Philadelphia

10h 53m2 stops Fort Lauderdale Tampa

$315Multiple Airlines

Mon, Aug 24 - Tue, Sep 22

7:03 am - 8:30 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 27mnonstop

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

2h 09mnonstop

$327American Airlines

Fri, Aug 21 - Mon, Sep 21

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

1h 55mnonstop

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

1h 55mnonstop

$327Southwest

Fri, Aug 21 - Mon, Sep 21

4:50 pm - 7:35 pmBWI Baltimore/Washington-MDW Chicago Midway

3h 45m1 stop Greater Rochester Intl

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

1h 55mnonstop

$333Southwest

Sun, Aug 23 - Mon, Sep 21

7:46 am - 9:00 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 14mnonstop

5:00 pm - 8:09 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 09mnonstop

$349United Airlines

Sun, Aug 23 - Mon, Sep 21

10:35 am - 11:53 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 18mnonstop

6:25 am - 9:23 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

1h 58mnonstop

$349United Airlines

Fri, Aug 21 - Sun, Sep 20

6:24 am - 1:20 pmBWI Baltimore/Washington-ORD Chicago O'Hare Intl

7h 56m1 stop Orlando

8:14 pm - 9:25 amORD Chicago O'Hare Intl-BWI Baltimore/Washington

36h 11m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson

$399Multiple Airlines

Recent direct flight deals from Maryland to Chicago

Fri, Oct 30 - Sun, Nov 1

11:05 am - 12:41 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

6:50 am - 10:00 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 10mnonstop

$167Frontier

Thu, Oct 8 - Sat, Oct 10

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

$168Frontier

Sat, Oct 10 - Mon, Oct 12

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

$168Frontier

Thu, Oct 8 - Mon, Oct 12

6:10 am - 7:25 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 15mnonstop

9:52 pm - 12:58 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 06mnonstop

$191United Airlines

Tue, Oct 6 - Mon, Oct 12

7:05 pm - 8:24 pmBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 19mnonstop

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

2h 00mnonstop

$192United Airlines

Sat, Sep 12 - Sat, Sep 19

8:40 am - 10:10 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 30mnonstop

6:55 pm - 10:00 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 05mnonstop

$197American Airlines

Thu, Oct 15 - Mon, Oct 19

7:45 am - 9:11 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 26mnonstop

5:59 am - 9:14 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 15mnonstop

$197American Airlines

Sat, Oct 10 - Mon, Oct 12

10:18 pm - 11:31 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 13mnonstop

9:52 pm - 12:58 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 06mnonstop

$198United Airlines

Sat, Oct 10 - Mon, Oct 12

5:45 pm - 6:45 pmBWI Baltimore/Washington-MDW Chicago Midway

2h 00mnonstop

5:00 am - 7:45 amMDW Chicago Midway-BWI Baltimore/Washington

1h 45mnonstop

$201Southwest

Sat, Oct 10 - Mon, Oct 12

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

2h 00mnonstop

5:00 am - 7:45 amMDW Chicago Midway-BWI Baltimore/Washington

1h 45mnonstop

$201Southwest

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 18% 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

Chesterton

Munster

Schererville

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

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Flights to other cities

Origins

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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 $158

$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