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

Fri, Jan 22 - Sun, Jan 24

12:46 pm - 2:19 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 33mnonstop

5:32 pm - 12:28 amORD Chicago O'Hare Intl-PHL Philadelphia

5h 56m1 stop Atlanta Hartsfield-Jackson

$177Frontier

Tue, Oct 6 - Tue, Oct 13

1:55 pm - 3:20 pmBWI Baltimore/Washington-ORD Chicago O'Hare Intl

26h 25m1 stop Fort Lauderdale

6:00 am - 2:20 pmORD Chicago O'Hare Intl-BWI Baltimore/Washington

31h 20m2 stops Atlanta Hartsfield-Jackson Orlando

$177Frontier

Sat, Nov 7 - Tue, Nov 10

12:20 pm - 4:26 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

5h 06m1 stop Detroit Metropolitan Wayne County

5:05 pm - 11:21 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

5h 16m1 stop Detroit Metropolitan Wayne County

$179Delta

Tue, Oct 20 - Sat, Oct 24

3:03 pm - 8:38 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

6h 35m1 stop Atlanta Hartsfield-Jackson

6:08 pm - 12:42 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

5h 34m1 stop Atlanta Hartsfield-Jackson

$179Delta

Sat, Oct 31 - Sat, Nov 7

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

2h 44mnonstop

7:29 pm - 10:53 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 24mnonstop

$185American Airlines

Sat, Oct 10 - Tue, Oct 13

3:51 pm - 5:34 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 43mnonstop

6:29 am - 9:40 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 11mnonstop

$185American Airlines

Tue, Nov 17 - Wed, Nov 18

10:54 am - 12:29 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 35mnonstop

6:24 pm - 9:38 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 14mnonstop

$185United Airlines

Wed, Oct 28 - Sat, Oct 31

6:15 am - 7:51 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

8:50 am - 12:04 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 14mnonstop

$185United Airlines

Wed, Nov 18 - Wed, Nov 18

7:30 am - 8:50 amPHL Philadelphia-MDW Chicago Midway

2h 20mnonstop

11:25 am - 2:15 pmMDW Chicago Midway-PHL Philadelphia

1h 50mnonstop

$185Southwest

Tue, Nov 10 - Sat, Nov 14

7:30 am - 8:50 amPHL Philadelphia-MDW Chicago Midway

2h 20mnonstop

7:45 am - 10:45 amMDW Chicago Midway-PHL Philadelphia

2h 00mnonstop

$185Southwest

Recent last minute flight deals from Maryland to Chicago

Thu, Sep 24 - Sat, Oct 10

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

2h 36mnonstop

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

2h 23mnonstop

$219Frontier

Fri, Sep 25 - Sat, Oct 10

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

2h 36mnonstop

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

2h 23mnonstop

$235Frontier

Tue, Sep 22 - Fri, Sep 25

5:35 pm - 6:55 pmBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 20mnonstop

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

2h 09mnonstop

$239United Airlines

Sat, Sep 26 - Sat, Oct 10

8:50 am - 2:29 pmPHL Philadelphia-ORD Chicago O'Hare Intl

6h 39m1 stop Atlanta Hartsfield-Jackson

5:29 pm - 11:08 pmORD Chicago O'Hare Intl-PHL Philadelphia

4h 39m1 stop Detroit Metropolitan Wayne County

$346Delta

Wed, Sep 23 - Sun, Oct 25

7:55 am - 8:55 amPHL Philadelphia-MDW Chicago Midway

2h 00mnonstop

8:15 pm - 11:15 pmMDW Chicago Midway-PHL Philadelphia

2h 00mnonstop

$353Southwest

Wed, Sep 23 - Sun, Oct 25

5:49 pm - 7:39 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 50mnonstop

6:29 am - 9:40 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 11mnonstop

$353American Airlines

Wed, Sep 23 - Sun, Oct 25

7:55 am - 8:55 amPHL Philadelphia-MDW Chicago Midway

2h 00mnonstop

5:25 pm - 1:00 amMDW Chicago Midway-PHL Philadelphia

6h 35m1 stop Orlando

$363Southwest

Wed, Sep 23 - Sun, Oct 25

12:04 pm - 4:00 pmPHL Philadelphia-ORD Chicago O'Hare Intl

4h 56m1 stop Charlotte Douglas

9:00 pm - 12:12 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 12mnonstop

$363American Airlines

Tue, Sep 22 - Tue, Sep 22

6:25 am - 7:50 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 25mnonstop

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

2h 18mnonstop

$390United Airlines

Tue, Sep 22 - Tue, Sep 22

6:30 am - 11:54 amPHL Philadelphia-MDW Chicago Midway

6h 24m1 stop Atlanta Hartsfield-Jackson

5:11 pm - 12:40 amMDW Chicago Midway-PHL Philadelphia

6h 29m1 stop Atlanta Hartsfield-Jackson

$415Delta

Recent direct flight deals from Maryland to Chicago

Fri, Oct 23 - Thu, Oct 29

9:58 am - 11:21 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 23mnonstop

6:00 am - 8:57 amORD Chicago O'Hare Intl-BWI Baltimore/Washington

1h 57mnonstop

$177Frontier

Thu, Oct 8 - Mon, Oct 12

9:58 am - 11:21 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 23mnonstop

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

2h 03mnonstop

$178Frontier

Thu, Oct 15 - Fri, Oct 16

9:58 am - 11:21 amBWI Baltimore/Washington-ORD Chicago O'Hare Intl

2h 23mnonstop

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

2h 03mnonstop

$178Frontier

Sat, Oct 31 - Sat, Nov 7

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

2h 44mnonstop

7:29 pm - 10:53 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 24mnonstop

$185American Airlines

Wed, Oct 21 - Sat, Oct 24

7:25 am - 9:00 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 35mnonstop

9:00 pm - 12:12 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 12mnonstop

$185American Airlines

Tue, Nov 17 - Wed, Nov 18

10:54 am - 12:29 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 35mnonstop

6:24 pm - 9:38 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 14mnonstop

$185United Airlines

Wed, Oct 28 - Sat, Oct 31

6:15 am - 7:51 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

8:50 am - 12:04 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 14mnonstop

$185United Airlines

Wed, Dec 2 - Wed, Dec 9

6:20 pm - 7:35 pmPHL Philadelphia-MDW Chicago Midway

2h 15mnonstop

8:10 am - 11:05 amMDW Chicago Midway-PHL Philadelphia

1h 55mnonstop

$185Southwest

Tue, Nov 17 - Wed, Nov 18

7:30 am - 8:50 amPHL Philadelphia-MDW Chicago Midway

2h 20mnonstop

11:25 am - 2:15 pmMDW Chicago Midway-PHL Philadelphia

1h 50mnonstop

$185Southwest

Sat, Oct 10 - Tue, Oct 13

3:51 pm - 5:34 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 43mnonstop

6:29 am - 9:40 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 11mnonstop

$185American Airlines

Useful Info

Low season	February
High season	July
Cheapest flight	$89

Best time to beat the crowds with an average 22% drop in price.

Most popular time to fly with an average 18% increase in price.

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

Hammond

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

Chesterton

Munster

Porter

Monticello

Saint John

Griffith

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$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

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Cheapest flight

FAQs for booking flights from Maryland to Chicago

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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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Flights to other popular destinations

Find deals for your return flight