Flights from Chicago (MDW)

Watch this city: Get top deals and price alerts from Chicago (MDW)
Search Cheap Flights from Chicago

Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.

Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.

Send me great deals:
By proceeding, you agree to our Privacy and Cookies Statement and Terms of Use
Sort By: Price ↑
Airlines
Stops
Fare Type
Nearby Airports
When to Travel
Chicago, IL (MDW) to
Detroit, MI (DTW)
Watch this route 
$97RT
Nonstop
Chicago, IL (MDW)toDetroit, MI (DTW)
Best Times to Go
Delta
$186RT
Nonstop|Weekend Deal
Chicago, IL (MDW)toDetroit, MI (DTW)
Thu, May 1 - Sun, May 4
Delta
$201RT
Nonstop|Weekend Deal
Chicago, IL (MDW)toDetroit, MI (DTW)
Fri, Jun 6 - Sun, Jun 8
Delta
See more deals to Detroit, MI (DTW)
Chicago, IL (MDW) to
Minneapolis, MN (MSP)
Watch this route 
$97RT
Nonstop|Midweek Fare
Chicago, IL (MDW)toMinneapolis, MN (MSP)
Best Times to Go
Delta
$127RT
Nonstop
Chicago, IL (MDW)toMinneapolis, MN (MSP)
Mon, Apr 28 - Mon, May 5
Delta
$172RT
Nonstop
Chicago, IL (MDW)toMinneapolis, MN (MSP)
Sat, Apr 19 - Mon, Apr 21
Delta
See more deals to Minneapolis, MN (MSP)
Chicago, IL (MDW) to
Orlando, FL (MCO)
Watch this route 
$116RT
Nonstop
Chicago, IL (MDW)toOrlando, FL (MCO)
Best Times to Go
Frontier
$230RT
Nonstop
Chicago, IL (MDW)toOrlando, FL (MCO)
Fri, Jun 13 - Fri, Jun 20
Frontier
$232RT
Nonstop
Chicago, IL (MDW)toOrlando, FL (MCO)
Sun, Apr 27 - Sun, May 4
Frontier
See more deals to Orlando, FL (MCO)
Chicago, IL (MDW) to
Dallas, TX (DFW)
Watch this route 
$116RT
Nonstop
Chicago, IL (MDW)toDallas/Fort Worth, TX (DFW)
Fri, Apr 25 - Fri, May 2
Frontier
$142RT
Nonstop
Chicago, IL (MDW)toDallas/Fort Worth, TX (DFW)
Best Times to Go
Frontier
$148RT
Nonstop|Midweek Fare
Chicago, IL (MDW)toDallas/Fort Worth, TX (DFW)
Wed, Jun 11 - Wed, Jun 18
Frontier
See more deals to Dallas, TX (DFW)
Chicago, IL (MDW) to
Atlanta, GA (ATL)
Watch this route 
$128RT
Nonstop|Midweek Fare
Chicago, IL (MDW)toAtlanta, GA (ATL)
Best Times to Go
Frontier
$130RT
Nonstop
Chicago, IL (MDW)toAtlanta, GA (ATL)
Sat, Jun 21 - Sat, Jun 28
Frontier
$160RT
Nonstop|Weekend Deal
Chicago, IL (MDW)toAtlanta, GA (ATL)
Fri, May 30 - Mon, Jun 2
Frontier
See more deals to Atlanta, GA (ATL)
Chicago, IL (MDW) to
Baltimore, MD (BWI)
Watch this route 
$137RT
Nonstop|Midweek Fare
Chicago, IL (MDW)toBaltimore, MD (BWI)
Best Times to Go
Frontier
$168RT
Nonstop
Chicago, IL (MDW)toBaltimore, MD (BWI)
Mon, Apr 28 - Mon, May 5
Frontier
$190RT
Nonstop|Midweek Fare
Chicago, IL (MDW)toBaltimore, MD (BWI)
Wed, Jun 18 - Wed, Jun 25
Frontier
See more deals to Baltimore, MD (BWI)
Chicago, IL (MDW) to
Denver, CO (DEN)
Watch this route 
$140RT
Nonstop
Chicago, IL (MDW)toDenver, CO (DEN)
Best Times to Go
Frontier
$170RT
Nonstop
Chicago, IL (MDW)toDenver, CO (DEN)
Sat, Jun 14 - Sat, Jun 21
Frontier
$216RT
Weekend Deal
Chicago, IL (MDW)toDenver, CO (DEN)
Fri, Apr 18 - Mon, Apr 21
Delta
See more deals to Denver, CO (DEN)
Chicago, IL (MDW) to
Houston, TX (IAH)
Watch this route 
$148RT
Nonstop|Midweek Fare
Chicago, IL (MDW)toHouston, TX (IAH)
Best Times to Go
Frontier
$190RT
Nonstop|Midweek Fare
Chicago, IL (MDW)toHouston, TX (IAH)
Wed, Jun 18 - Wed, Jun 25
Frontier
See more deals to Houston, TX (IAH)
Chicago, IL (MDW) to
Philadelphia, PA (PHL)
Watch this route 
$150RT
Nonstop
Chicago, IL (MDW)toPhiladelphia, PA (PHL)
Best Times to Go
Frontier
$199RT
Nonstop|Weekend Deal
Chicago, IL (MDW)toPhiladelphia, PA (PHL)
Thu, Apr 17 - Sun, Apr 20
Frontier
$239RT
Nonstop
Chicago, IL (MDW)toPhiladelphia, PA (PHL)
Mon, Apr 28 - Mon, May 5
Frontier
See more deals to Philadelphia, PA (PHL)
Chicago, IL (MDW) to
Tampa, FL (TPA)
Watch this route 
$154RT
Nonstop|Midweek Fare
Chicago, IL (MDW)toTampa, FL (TPA)
Best Times to Go
Frontier
$162RT
Nonstop
Chicago, IL (MDW)toTampa, FL (TPA)
Sat, Apr 19 - Mon, Apr 21
Frontier
$178RT
Nonstop
Chicago, IL (MDW)toTampa, FL (TPA)
Sat, Apr 5 - Mon, Apr 7
Frontier
See more deals to Tampa, FL (TPA)
Chicago, IL (MDW) to
Boston, MA (BOS)
Watch this route 
$170RT
Midweek Fare
Chicago, IL (MDW)toBoston, MA (BOS)
Best Times to Go
Delta
$200RT
Weekend Deal
Chicago, IL (MDW)toBoston, MA (BOS)
Fri, May 2 - Mon, May 5
Delta
$208RT
Chicago, IL (MDW)toBoston, MA (BOS)
Fri, Jun 6 - Wed, Jun 11
Delta
See more deals to Boston, MA (BOS)
Chicago, IL (MDW) to
Cincinnati, OH (CVG)
Watch this route 
$170RT
Midweek Fare
Chicago, IL (MDW)toCincinnati, OH (CVG)
Tue, Jun 3 - Tue, Jun 10
Frontier
See more deals to Cincinnati, OH (CVG)
Chicago, IL (MDW) to
Nashville, TN (BNA)
Watch this route 
$176RT
Midweek Fare
Chicago, IL (MDW)toNashville, TN (BNA)
Best Times to Go
Delta
$246RT
Midweek Fare
Chicago, IL (MDW)toNashville, TN (BNA)
Tue, Jun 10 - Tue, Jun 17
Delta
See more deals to Nashville, TN (BNA)
Chicago, IL (MDW) to
Pittsburgh, PA (PIT)
Watch this route 
$176RT
Chicago, IL (MDW)toPittsburgh, PA (PIT)
Best Times to Go
Delta
See more deals to Pittsburgh, PA (PIT)
Chicago, IL (MDW) to
Grand Rapids, MI (GRR)
Watch this route 
$176RT
Midweek Fare
Chicago, IL (MDW)toGrand Rapids, MI (GRR)
Wed, May 14 - Wed, May 21
Delta
See more deals to Grand Rapids, MI (GRR)
Chicago, IL (MDW) to
Saint Louis, MO (STL)
Watch this route 
$176RT
Midweek Fare
Chicago, IL (MDW)toSaint Louis, MO (STL)
Best Times to Go
Delta
See more deals to Saint Louis, MO (STL)
Chicago, IL (MDW) to
Louisville, KY (SDF)
Watch this route 
$176RT
Chicago, IL (MDW)toLouisville, KY (SDF)
Sat, May 3 - Sat, May 10
Delta
See more deals to Louisville, KY (SDF)
Chicago, IL (MDW) to
Fort Walton Beach, FL (VPS)
Watch this route 
$177RT
Midweek Fare
Chicago, IL (MDW)toValparaiso, FL (VPS)
Tue, Jun 10 - Tue, Jun 17
Delta
See more deals to Fort Walton Beach, FL (VPS)
Chicago, IL (MDW) to
Newark, NJ (EWR)
Watch this route 
$178RT
Chicago, IL (MDW)toNewark, NJ (EWR)
Best Times to Go
Delta
$196RT
Chicago, IL (MDW)toNewark, NJ (EWR)
Sat, May 31 - Tue, Jun 3
Delta
$197RT
Chicago, IL (MDW)toNewark, NJ (EWR)
Wed, Apr 30 - Sun, May 4
Delta
See more deals to Newark, NJ (EWR)
Chicago, IL (MDW) to
Cleveland, OH (CLE)
Watch this route 
$190RT
Midweek Fare
Chicago, IL (MDW)toCleveland, OH (CLE)
Best Times to Go
Frontier
$228RT
Midweek Fare
Chicago, IL (MDW)toCleveland, OH (CLE)
Thu, May 22 - Thu, May 29
Frontier
$256RT
Chicago, IL (MDW)toCleveland, OH (CLE)
Mon, Apr 28 - Mon, May 5
Delta
See more deals to Cleveland, OH (CLE)
Chicago, IL (MDW) to
Phoenix, AZ (PHX)
Watch this route 
$196RT
Nonstop
Chicago, IL (MDW)toPhoenix, AZ (PHX)
Best Times to Go
Frontier
$244RT
Nonstop|Midweek Fare
Chicago, IL (MDW)toPhoenix, AZ (PHX)
Thu, Jun 5 - Thu, Jun 12
Frontier
See more deals to Phoenix, AZ (PHX)
Chicago, IL (MDW) to
Charlotte, NC (CLT)
Watch this route 
$196RT
Chicago, IL (MDW)toCharlotte, NC (CLT)
Best Times to Go
Delta
$216RT
Chicago, IL (MDW)toCharlotte, NC (CLT)
Sat, May 10 - Tue, May 13
Delta
See more deals to Charlotte, NC (CLT)
Chicago, IL (MDW) to
Washington DC, DC (DCA)
Watch this route 
$196RT
Midweek Fare
Chicago, IL (MDW)toWashington, DC (DCA)
Best Times to Go
Delta
$216RT
Weekend Deal
Chicago, IL (MDW)toWashington, DC (DCA)
Fri, May 9 - Mon, May 12
Delta
$222RT
Weekend Deal
Chicago, IL (MDW)toWashington, DC (DCA)
Best Times to Go
Delta
See more deals to Washington DC, DC (DCA)
Chicago, IL (MDW) to
Washington DC, DC (IAD)
Watch this route 
$196RT
Midweek Fare
Chicago, IL (MDW)toWashington, DC (IAD)
Best Times to Go
Delta
$216RT
Weekend Deal
Chicago, IL (MDW)toWashington, DC (IAD)
Fri, May 9 - Mon, May 12
Delta
$222RT
Chicago, IL (MDW)toWashington, DC (IAD)
Fri, Jun 6 - Wed, Jun 11
Delta
See more deals to Washington DC, DC (IAD)
Chicago, IL (MDW) to
Miami, FL (MIA)
Watch this route 
$202RT
Nonstop
Chicago, IL (MDW)toMiami, FL (MIA)
Sat, Apr 5 - Tue, Apr 8
Frontier
$260RT
Chicago, IL (MDW)toMiami, FL (MIA)
Best Times to Go
Delta
See more deals to Miami, FL (MIA)
Chicago, IL (MDW) to
Las Vegas, NV (LAS)
Watch this route 
$206RT
Nonstop
Chicago, IL (MDW)toLas Vegas, NV (LAS)
Sat, Apr 12 - Mon, Apr 14
Frontier
$218RT
Nonstop
Chicago, IL (MDW)toLas Vegas, NV (LAS)
Fri, Apr 25 - Fri, May 2
Frontier
$255RT
Nonstop|Weekend Deal
Chicago, IL (MDW)toLas Vegas, NV (LAS)
Fri, Apr 18 - Mon, Apr 21
Frontier
See more deals to Las Vegas, NV (LAS)
Chicago, IL (MDW) to
Greenville, SC (GSP)
Watch this route 
$214RT
Chicago, IL (MDW)toGreenville, SC (GSP)
Best Times to Go
Delta
See more deals to Greenville, SC (GSP)
Chicago, IL (MDW) to
Boise, ID (BOI)
Watch this route 
$216RT
Chicago, IL (MDW)toBoise, ID (BOI)
Mon, May 5 - Tue, May 13
Delta
See more deals to Boise, ID (BOI)
Chicago, IL (MDW) to
Fort Myers, FL (RSW)
Watch this route 
$216RT
Chicago, IL (MDW)toFort Myers, FL (RSW)
Best Times to Go
Delta
$236RT
Weekend Deal
Chicago, IL (MDW)toFort Myers, FL (RSW)
Fri, Jul 4 - Tue, Jul 8
Delta
See more deals to Fort Myers, FL (RSW)
Chicago, IL (MDW) to
West Palm Beach, FL (PBI)
Watch this route 
$216RT
Chicago, IL (MDW)toWest Palm Beach, FL (PBI)
Best Times to Go
Delta
See more deals to West Palm Beach, FL (PBI)
Chicago, IL (MDW) to
Austin, TX (AUS)
Watch this route 
$216RT
Midweek Fare
Chicago, IL (MDW)toAustin, TX (AUS)
Best Times to Go
Delta
$226RT
Weekend Deal
Chicago, IL (MDW)toAustin, TX (AUS)
Best Times to Go
Delta
See more deals to Austin, TX (AUS)
Chicago, IL (MDW) to
Dallas, TX (DAL)
Watch this route 
$216RT
Chicago, IL (MDW)toDallas, TX (DAL)
Best Times to Go
Delta
See more deals to Dallas, TX (DAL)
Chicago, IL (MDW) to
Panama City, FL (ECP)
Watch this route 
$222RT
Midweek Fare
Chicago, IL (MDW)toPanama City, FL (ECP)
Best Times to Go
Delta
See more deals to Panama City, FL (ECP)
Chicago, IL (MDW) to
Buffalo, NY (BUF)
Watch this route 
$228RT
Chicago, IL (MDW)toBuffalo, NY (BUF)
Best Times to Go
Frontier
See more deals to Buffalo, NY (BUF)
Chicago, IL (MDW) to
Memphis, TN (MEM)
Watch this route 
$236RT
Midweek Fare
Chicago, IL (MDW)toMemphis, TN (MEM)
Best Times to Go
Delta
See more deals to Memphis, TN (MEM)
Chicago, IL (MDW) to
San Antonio, TX (SAT)
Watch this route 
$236RT
Weekend Deal
Chicago, IL (MDW)toSan Antonio, TX (SAT)
Best Times to Go
Delta
See more deals to San Antonio, TX (SAT)
Chicago, IL (MDW) to
New York City, NY (JFK)
Watch this route 
$247RT
Weekend Deal
Chicago, IL (MDW)toNew York, NY (JFK)
Best Times to Go
Delta
See more deals to New York City, NY (JFK)
Chicago, IL (MDW) to
Raleigh, NC (RDU)
Watch this route 
$248RT
Chicago, IL (MDW)toRaleigh/Durham, NC (RDU)
Best Times to Go
Frontier
$250RT
Midweek Fare
Chicago, IL (MDW)toRaleigh/Durham, NC (RDU)
Tue, Jun 10 - Tue, Jun 17
Frontier
See more deals to Raleigh, NC (RDU)
Chicago, IL (MDW) to
New York City, NY (LGA)
Watch this route 
$248RT
Midweek Fare
Chicago, IL (MDW)toNew York, NY (LGA)
Best Times to Go
Frontier
See more deals to New York City, NY (LGA)
Chicago, IL (MDW) to
Providence, RI (PVD)
Watch this route 
$256RT
Midweek Fare
Chicago, IL (MDW)toProvidence, RI (PVD)
Best Times to Go
Delta
See more deals to Providence, RI (PVD)
Chicago, IL (MDW) to
El Paso, TX (ELP)
Watch this route 
$256RT
Midweek Fare
Chicago, IL (MDW)toEl Paso, TX (ELP)
Best Times to Go
Delta
See more deals to El Paso, TX (ELP)
Chicago, IL (MDW) to
Burbank, CA (BUR)
Watch this route 
$256RT
Chicago, IL (MDW)toBurbank, CA (BUR)
Best Times to Go
Delta
See more deals to Burbank, CA (BUR)
Chicago, IL (MDW) to
San Francisco, CA (SFO)
Watch this route 
$256RT
Chicago, IL (MDW)toSan Francisco, CA (SFO)
Best Times to Go
Delta
See more deals to San Francisco, CA (SFO)
Chicago, IL (MDW) to
Columbus, OH (CMH)
Watch this route 
$256RT
Midweek Fare
Chicago, IL (MDW)toColumbus, OH (CMH)
Best Times to Go
Delta
See more deals to Columbus, OH (CMH)
Load More Flight Deals

More Flight Deals from Chicago