$99 Find Cheap Flights from Maryland to Chicago - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 9/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Flight Deals

Cheap Flights from Maryland to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Maryland to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Maryland to Chicago

Thu, Sep 3 - Sun, Sep 6
Frontier Logo
8:30 am - 7:59 pm
PHL
-
ORD
12h 29m
1 stop
Frontier Logo
6:00 am - 9:17 am
ORD
-
PHL
2h 17mnonstop
$213Frontier
Wed, Aug 19 - Tue, Aug 25
Southwest Logo
7:15 am - 3:25 pm
PHL
-
MDW
9h 10m
2 stops
Southwest Logo
12:35 pm - 9:50 pm
MDW
-
PHL
8h 15m
2 stops
$213Southwest
Sat, Aug 29 - Mon, Aug 31
American Airlines Logo
3:25 pm - 6:54 pm
PHL
-
ORD
4h 29m
1 stop
American Airlines Logo
4:00 pm - 7:19 pm
ORD
-
PHL
2h 19mnonstop
$219American Airlines
Thu, Aug 6 - Tue, Aug 11
Multiple Airlines Logo
7:00 am - 8:52 pm
DCA
-
ORD
14h 52m
1 stop
Multiple Airlines Logo
11:01 am - 7:05 pm
ORD
-
DCA
7h 04m
1 stop
$240Multiple Airlines
Sat, Oct 10 - Tue, Oct 13
American Airlines Logo
6:00 am - 7:27 am
DCA
-
ORD
2h 27mnonstop
American Airlines Logo
8:58 pm - 11:59 pm
ORD
-
DCA
2h 01mnonstop
$241American Airlines
Thu, Sep 24 - Sun, Sep 27
Multiple Airlines Logo
6:30 am - 11:47 am
DCA
-
ORD
6h 17m
1 stop
Multiple Airlines Logo
11:06 am - 9:58 pm
ORD
-
DCA
9h 52m
1 stop
$242Multiple Airlines
Fri, Sep 4 - Mon, Sep 7
United Airlines Logo
2:00 pm - 3:16 pm
DCA
-
ORD
2h 16mnonstop
United Airlines Logo
7:00 am - 9:59 am
ORD
-
DCA
1h 59mnonstop
$243United Airlines
Fri, Aug 14 - Mon, Aug 17
United Airlines Logo
5:15 pm - 6:37 pm
IAD
-
ORD
2h 22mnonstop
United Airlines Logo
9:39 pm - 12:44 am
ORD
-
IAD
2h 05mnonstop
$243United Airlines
Mon, Aug 24 - Mon, Aug 31
JetBlue Logo
11:00 am - 7:27 pm
DCA
-
ORD
9h 27m
1 stop
JetBlue Logo
8:20 pm - 7:58 am
ORD
-
DCA
10h 38m
1 stop
$244JetBlue
Fri, Sep 4 - Sun, Sep 6
JetBlue Logo
2:00 pm - 7:26 pm
DCA
-
ORD
6h 26m
1 stop
JetBlue Logo
10:56 am - 5:56 pm
ORD
-
DCA
6h 00m
1 stop
$248JetBlue
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$99
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 19% lower on average.
Flight from Reagan Washington National Airport to Chicago O'Hare Airport

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?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Schererville
Munster
Chesterton
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Maryland

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights to Chicagofrom $566
Business Class flights to Chicagofrom $401
Premium Economy Class flights to Chicagofrom $375
Economy Class flights to Chicagofrom $208