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>

$92 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

Sat, May 23 - Sat, May 30

7:00 am - 11:01 pm

PHL

ORD

17h 01m

1 stop

7:52 pm - 11:18 pm

ORD

PHL

2h 26mnonstop

$185Frontier

Tue, May 26 - Tue, Jun 2

6:30 am - 11:12 am

PHL

MDW

5h 42m

1 stop

12:27 pm - 7:10 pm

MDW

PHL

5h 43m

1 stop

$185Frontier

Wed, May 27 - Thu, Jun 4

6:20 pm - 7:30 pm

BWI

MDW

2h 10mnonstop

7:00 pm - 9:55 pm

MDW

BWI

1h 55mnonstop

$212Southwest

Wed, May 27 - Thu, Jun 4

8:25 am - 9:39 am

BWI

ORD

2h 14mnonstop

6:20 pm - 9:26 pm

ORD

BWI

2h 06mnonstop

$212United Airlines

Wed, Jun 24 - Wed, Jun 24

7:50 am - 11:00 am

BWI

MDW

4h 10m

1 stop

12:00 pm - 5:35 pm

MDW

BWI

4h 35m

1 stop

$217Southwest

Tue, May 26 - Sat, May 30

6:00 am - 8:45 am

IAD

ORD

3h 45m

1 stop

12:00 pm - 8:02 pm

ORD

IAD

7h 02m

1 stop

$228Delta

Tue, May 26 - Mon, Jun 1

6:08 am - 10:00 am

IAD

MDW

4h 52m

1 stop

6:23 am - 2:10 pm

MDW

IAD

6h 47m

1 stop

$228Delta

Wed, Jun 10 - Sun, Jun 14

8:00 am - 10:37 am

PHL

RFD

27h 37m

1 stop

11:27 am - 12:44 am

RFD

PHL

12h 17m

1 stop

$229Multiple Airlines

Wed, Jul 1 - Sat, Aug 15

8:10 pm - 9:32 pm

DCA

ORD

2h 22mnonstop

4:00 pm - 6:52 pm

ORD

DCA

1h 52mnonstop

$233United Airlines

Wed, Jul 29 - Sun, Aug 2

1:10 pm - 10:37 am

BWI

RFD

22h 27m

1 stop

11:27 am - 7:36 am

RFD

BWI

19h 09m

2 stops

$281Multiple Airlines

Useful Info

Low season	February
High season	July
Cheapest flight	$92

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

Most popular time to fly with an average 3% 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 $718

Premium Economy Class flights to Chicagofrom $375

Economy Class flights to Chicagofrom $195

$92 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