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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

$93 CHEAP FLIGHTS from Maryland to Chicago

KAYAK searches hundreds of travel sites at once for deals on flights 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, Jul 23 - Sat, Jul 25

5:18 pm - 7:00 pm

PHL

ORD

2h 42mnonstop

8:05 pm - 11:31 pm

ORD

PHL

2h 26mnonstop

$189Frontier

Tue, Jun 9 - Wed, Jun 10

8:30 am - 7:53 pm

PHL

ORD

12h 23m

1 stop

1:29 pm - 10:29 pm

ORD

PHL

8h 00m

1 stop

$190Frontier

Tue, Aug 18 - Tue, Sep 1

6:32 pm - 7:59 pm

BWI

ORD

2h 27mnonstop

2:53 pm - 6:00 pm

ORD

BWI

2h 07mnonstop

$220American Airlines

Tue, Jun 23 - Tue, Jun 30

8:30 pm - 9:35 pm

BWI

MDW

2h 05mnonstop

7:50 am - 12:00 pm

MDW

BWI

3h 10m

1 stop

$226Southwest

Wed, Jun 3 - Sat, Jun 6

6:30 am - 7:35 am

BWI

MDW

2h 05mnonstop

10:20 am - 2:30 pm

MDW

BWI

3h 10m

1 stop

$228Southwest

Thu, Jul 9 - Sun, Jul 12

7:49 am - 10:08 pm

IAD

MDW

15h 19m

1 stop

2:48 pm - 2:26 pm

MDW

IAD

22h 38m

1 stop

$233Multiple Airlines

Thu, Jul 23 - Sun, Jul 26

11:17 am - 10:08 pm

IAD

MDW

11h 51m

1 stop

2:48 pm - 2:26 pm

MDW

IAD

22h 38m

1 stop

$236Multiple Airlines

Tue, Jun 30 - Tue, Jul 7

10:20 pm - 11:31 pm

IAD

ORD

2h 11mnonstop

1:30 pm - 4:30 pm

ORD

IAD

2h 00mnonstop

$237United Airlines

Thu, Aug 13 - Sat, Aug 15

6:10 pm - 7:33 pm

DCA

ORD

2h 23mnonstop

7:45 pm - 10:52 pm

ORD

DCA

2h 07mnonstop

$239United Airlines

Fri, Jul 3 - Wed, Jul 8

3:57 pm - 5:29 pm

DCA

ORD

2h 32mnonstop

5:58 am - 9:15 am

ORD

DCA

2h 17mnonstop

$243American Airlines

Useful Info

Low season	February
High season	July
Cheapest flight	$93

Best time to beat the crowds with an average 11% drop in price.

Most popular time to fly with an average 4% increase in price.

Flight from Philadelphia to Chicago Midway 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

Schererville

Munster

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

Cabin class

Complete your trip

Direct Flights

Flights to other cities

Origins

Other airports

Return flight deals

Cabin class types available on flights to Maryland

First Class flights to Chicagofrom $571

Business Class flights to Chicagofrom $728

Premium Economy Class flights to Chicagofrom $375

Economy Class flights to Chicagofrom $199

$93 Find Cheap Flights from Maryland to Chicago

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

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

FAQs for booking flights from Maryland to Chicago

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.

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