$89 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 9/5. 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

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Useful Info
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

Sun, Sep 20 - Wed, Sep 30
Frontier Logo
11:54 am - 1:30 pmPHL  Philadelphia-ORD Chicago O'Hare Intl
2h 36mnonstop
Frontier Logo
3:50 pm - 12:09 amORD  Chicago O'Hare Intl-PHL Philadelphia
7h 19m1 stop Orlando
$170Frontier
Sat, Sep 19 - Sat, Sep 26
Frontier Logo
8:41 am - 6:23 pmPHL  Philadelphia-ORD Chicago O'Hare Intl
10h 42m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
7:21 pm - 7:16 amORD  Chicago O'Hare Intl-PHL Philadelphia
10h 55m1 stop Atlanta Hartsfield-Jackson
$170Frontier
Fri, Sep 11 - Sun, Sep 13
Multiple Airlines Logo
11:54 am - 1:30 pmPHL  Philadelphia-ORD Chicago O'Hare Intl
2h 36mnonstop
Multiple Airlines Logo
3:00 pm - 11:07 pmORD  Chicago O'Hare Intl-PHL Philadelphia
7h 07m1 stop Fort Lauderdale
$171Multiple Airlines
Fri, Sep 11 - Sun, Sep 13
Multiple Airlines Logo
11:54 am - 1:30 pmPHL  Philadelphia-ORD Chicago O'Hare Intl
2h 36mnonstop
Multiple Airlines Logo
3:00 pm - 11:07 pmORD  Chicago O'Hare Intl-PHL Philadelphia
7h 07m1 stop Fort Lauderdale
$172Multiple Airlines
Fri, Sep 11 - Tue, Sep 15
Southwest Logo
9:15 pm - 10:15 pmDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
2h 00mnonstop
Southwest Logo
8:40 am - 3:50 pmMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
6h 10m2 stops Columbus Nashville Intl
$185Southwest
Fri, Sep 11 - Mon, Sep 14
American Airlines Logo
6:30 am - 7:58 amDCA  Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl
2h 28mnonstop
American Airlines Logo
6:55 am - 9:59 amORD  Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National
2h 04mnonstop
$185American Airlines
Thu, Sep 3 - Sun, Sep 6
United Airlines Logo
6:15 am - 7:30 amIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
2h 15mnonstop
United Airlines Logo
8:45 am - 11:52 amORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
2h 07mnonstop
$186United Airlines
Thu, Sep 3 - Sun, Sep 6
United Airlines Logo
8:30 am - 9:45 amDCA  Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl
2h 15mnonstop
United Airlines Logo
7:00 am - 9:59 amORD  Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National
1h 59mnonstop
$186United Airlines
Sun, Sep 6 - Fri, Sep 11
Southwest Logo
6:15 pm - 7:20 pmDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
2h 05mnonstop
Southwest Logo
3:10 pm - 10:45 pmMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
6h 35m1 stop Atlanta Hartsfield-Jackson
$187Southwest
Sat, Sep 26 - Tue, Sep 29
American Airlines Logo
7:39 pm - 9:30 pmPHL  Philadelphia-ORD Chicago O'Hare Intl
2h 51mnonstop
American Airlines Logo
5:00 am - 8:15 amORD  Chicago O'Hare Intl-PHL Philadelphia
2h 15mnonstop
$189American Airlines
Useful Info

Good to know

Low season

February

Cheapest flight

$89
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 18% lower on average.
Flight from Baltimore to Chicago Midway 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
Munster
Chesterton
Schererville
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 $437
Business Class flights to Chicagofrom $437
Premium Economy Class flights to Chicagofrom $375
Economy Class flights to Chicagofrom $163