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

Mon, Sep 21 - Thu, Sep 24

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

$166Frontier

Thu, Oct 22 - Sun, Oct 25

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

$167Frontier

Sat, Sep 19 - Tue, Sep 22

6:40 pm - 7:40 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 00mnonstop

11:10 am - 2:00 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$177Southwest

Wed, Sep 23 - Wed, Oct 14

9:00 pm - 10:10 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 10mnonstop

8:15 pm - 11:05 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$177Southwest

Wed, Oct 28 - Sat, Oct 31

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

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, Sep 19 - Sat, Sep 19

10:25 am - 11:45 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 20mnonstop

6:15 pm - 9:29 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 14mnonstop

$177United Airlines

Wed, Sep 30 - Mon, Oct 5

12:10 pm - 1:30 pmBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 20mnonstop

3:00 pm - 6:13 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 13mnonstop

$177United Airlines

Mon, Oct 12 - Mon, Oct 19

9:59 pm - 3:30 pmBWI Baltimore/Washington-ORD Chicago O'Hare Intl

42h 31m2 stops Tampa Fort Lauderdale

6:00 am - 9:03 amORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 03mnonstop

$193Multiple 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

$206Multiple Airlines

Recent last minute flight deals from Maryland to Chicago

Thu, Sep 3 - Sun, Sep 6

5:30 pm - 7:12 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 42mnonstop

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

2h 09mnonstop

$221Frontier

Thu, Sep 3 - Sun, Sep 6

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

$222Frontier

Wed, Sep 2 - Wed, Sep 30

3:41 pm - 5:14 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 33mnonstop

8:50 am - 11:54 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 04mnonstop

$335American Airlines

Wed, Sep 2 - Wed, Sep 30

6:15 am - 7:30 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 15mnonstop

12:55 pm - 4:01 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 06mnonstop

$337United Airlines

Wed, Sep 2 - Sun, Sep 6

5:40 pm - 7:00 pmBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 20mnonstop

7:45 pm - 11:00 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

2h 15mnonstop

$339United Airlines

Wed, Sep 2 - Wed, Sep 30

11:56 am - 4:00 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

5h 04m1 stop Charlotte Douglas

6:55 am - 9:59 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 04mnonstop

$345American Airlines

Wed, Sep 2 - Sun, Sep 6

2:50 pm - 3:50 pmBWI Baltimore/Washington-MDW Chicago Midway

2h 00mnonstop

1:30 pm - 6:10 pmMDW Chicago Midway-BWI Baltimore/Washington

3h 40m1 stop Columbus

$349Southwest

Tue, Sep 1 - Sun, Sep 6

6:25 pm - 7:30 pmPHL Philadelphia-MDW Chicago Midway

2h 05mnonstop

8:40 am - 11:45 amMDW Chicago Midway-PHL Philadelphia

2h 05mnonstop

$358Southwest

Wed, Sep 2 - Mon, Oct 5

12:36 pm - 4:17 pmPHL Philadelphia-ORD Chicago O'Hare Intl

4h 41m1 stop Detroit Metropolitan Wayne County

5:10 pm - 11:12 pmORD Chicago O'Hare Intl-PHL Philadelphia

5h 02m1 stop Detroit Metropolitan Wayne County

$388Delta

Wed, Sep 2 - Sun, Sep 6

6:05 am - 9:17 amPHL Philadelphia-MDW Chicago Midway

4h 12m1 stop Detroit Metropolitan Wayne County

6:05 am - 12:44 pmMDW Chicago Midway-PHL Philadelphia

5h 39m1 stop Atlanta Hartsfield-Jackson

$398Delta

Recent direct flight deals from Maryland to Chicago

Mon, Sep 21 - Thu, Sep 24

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

$166Frontier

Thu, Oct 22 - Sun, Oct 25

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

$167Frontier

Thu, Nov 12 - Sun, Nov 15

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

Wed, Oct 21 - Mon, Oct 26

10:20 am - 11:20 amBWI Baltimore/Washington-MDW Chicago Midway

2h 00mnonstop

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

1h 45mnonstop

$177Southwest

Thu, Nov 12 - Sat, Nov 14

12:35 pm - 1:40 pmBWI Baltimore/Washington-MDW Chicago Midway

2h 05mnonstop

4:25 pm - 7:15 pmMDW Chicago Midway-BWI Baltimore/Washington

1h 50mnonstop

$177Southwest

Thu, Nov 5 - Mon, Nov 9

8:23 am - 9:45 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 22mnonstop

8:50 am - 11:52 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 02mnonstop

$177United Airlines

Thu, Oct 22 - Sat, Oct 24

10:30 am - 11:48 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 18mnonstop

12:55 pm - 4:01 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 06mnonstop

$177United Airlines

Sat, Sep 26 - Sat, Oct 3

3:58 pm - 5:28 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 30mnonstop

6:55 am - 9:59 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 04mnonstop

$177American Airlines

Thu, Oct 15 - Mon, Oct 19

6:00 am - 7:27 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 27mnonstop

6:59 am - 10:06 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 07mnonstop

$177American Airlines

Wed, Sep 30 - Tue, Oct 6

2:50 pm - 3:50 pmBWI Baltimore/Washington-MDW Chicago Midway

2h 00mnonstop

3:20 pm - 6:05 pmMDW Chicago Midway-BWI Baltimore/Washington

1h 45mnonstop

$177Southwest

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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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 $118

$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