Cheap flights to Chicago, Illinois (MDW)

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Low Fares to Chicago, Illinois (MDW)

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$272 RT
Akron, OH (CAK) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$364 RT
Albany, NY (ALB) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$364 RT
Albany, NY (ALB) 330 day travel period. (Delta) See all details »
$338 RT
Albany, NY (ALB) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$398 RT
Albuquerque, NM (ABQ) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$284 RT
Asheville, NC (AVL) 330 day travel period.. No min. stay. (Delta) See all details »
$253 RT
Atlanta, GA (ATL) Non-Stop Flights.. No peak holiday travel at this price. (Delta) See all details »
$253 RT
Atlanta, GA (ATL) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$248 RT
Atlanta, GA (ATL) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$378 RT
Austin, TX (AUS) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$348 RT
Austin, TX (AUS) No min. stay. (Delta) See all details »
$362 RT
Austin, TX (AUS) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$268 RT
Baltimore, MD (BWI) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$326 RT
Baltimore, MD (BWI) Spring/Fall travel; Nonstop flights.. No min. stay.. Fare can be bought... (Southwest) See all details »
$342 RT
Baltimore, MD (BWI) 330 day travel period. (Delta) See all details »
$278 RT
Birmingham, AL (BHM) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$448 RT
Boise, ID (BOI) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$202 RT
Boston, MA (BOS) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$218 RT
Boston, MA (BOS) 330 day travel period.. No peak summer travel at this price. (Delta) See all details »
$218 RT
Boston, MA (BOS) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$218 RT
Buffalo, NY (BUF) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$234 RT
Buffalo, NY (BUF) No min. stay.. No peak summer travel at this price. (Delta) See all details »
$234 RT
Buffalo, NY (BUF) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$468 RT
Burbank, CA (BUR) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$286 RT
Charleston, SC (CHS) 330 day travel period.. No min. stay. (Delta) See all details »
$286 RT
Charleston, SC (CHS) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$286 RT
Charleston, SC (CHS) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$296 RT
Charlotte, NC (CLT) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$280 RT
Charlotte, NC (CLT) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$296 RT
Charlotte, NC (CLT) Travel through early January 2016. (Delta) See all details »
$378 RT
Cincinnati, OH (CVG) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$188 RT
Cleveland, OH (CLE) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$204 RT
Cleveland, OH (CLE) No min. stay.. No peak summer travel at this price. (Delta) See all details »
$204 RT
Cleveland, OH (CLE) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$258 RT
Columbia, SC (CAE) 330 day travel period. (Delta) See all details »
$210 RT
Columbus, OH (CMH) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$194 RT
Columbus, OH (CMH) Non-Stop Flights.. Travel through early January 2016.. No min. stay.. F... (Southwest) See all details »
$210 RT
Columbus, OH (CMH) Travel through early January 2016.. No min. stay.. No peak holiday trav... (Delta) See all details »
$194 RT
Dallas, TX (DFW) 330 day travel period.. No min. stay.. No peak holiday travel at this p... (Delta) See all details »
$184 RT
Dallas, TX (DAL) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$184 RT
Dallas, TX (DFW) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$286 RT
Daytona Beach, FL (DAB) 330 day travel period. (Delta) See all details »
$146 RT
Denver, CO (DEN) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$246 RT
Des Moines, IA (DSM) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$219 RT
Detroit, MI (DTW) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$220 RT
Detroit, MI (DTW) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$219 RT
Detroit, MI (DTW) Non-Stop Flights.. No min. stay. (Delta) See all details »
$390 RT
El Paso, TX (ELP) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$350 RT
Fayetteville, AR (XNA) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$184 RT
Ft. Lauderdale, FL (FLL) No min. stay.. Fare can be bought one-way for half the lowest roundtrip... (Southwest) See all details »
$184 RT
Ft. Lauderdale, FL (FLL) 330 day travel period.. No peak holiday travel at this price. (Delta) See all details »
$184 RT
Ft. Lauderdale, FL (FLL) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$320 RT
Ft. Myers, FL (RSW) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$338 RT
Ft. Myers, FL (RSW) 330 day travel period. (Delta) See all details »
$336 RT
Ft. Myers, FL (RSW) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$292 RT
Greensboro, NC (GSO) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$272 RT
Greenville, SC (GSP) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$231 RT
Greenville, SC (GSP) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$247 RT
Greenville, SC (GSP) No peak summer travel at this price. (Delta) See all details »
$372 RT
Harrisburg, PA (MDT) 330 day travel period. (Delta) See all details »
$344 RT
Hartford, CT (BDL) 330 day travel period.. No min. stay. (Delta) See all details »
$344 RT
Hartford, CT (BDL) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$344 RT
Hartford, CT (BDL) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$840 RT
Honolulu, HI (HNL) Late Summer/Fall travel.. Winter travel.. No peak holiday travel at thi... (Delta) See all details »
$158 RT
Houston, TX (HOU) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$184 RT
Houston, TX (IAH) 330 day travel period.. No peak holiday travel at this price. (Delta) See all details »
$184 RT
Houston, TX (HOU) No peak holiday travel at this price. (Delta) See all details »
$184 RT
Houston, TX (HOU) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$184 RT
Houston, TX (IAH) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$284 RT
Hudson Valley, NY (SWF) 330 day travel period.. No peak summer travel at this price.. No peak h... (Delta) See all details »
$256 RT
Indianapolis, IN (IND) 330 day travel period. (Delta) See all details »
$290 RT
Islip, NY (ISP) No min. stay.. Fare can be bought one-way for half the lowest roundtrip... (Southwest) See all details »
$340 RT
Jackson, MS (JAN) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$316 RT
Jacksonville, FL (JAX) 330 day travel period.. No min. stay. (Delta) See all details »
$316 RT
Jacksonville, FL (JAX) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$340 RT
Jacksonville, FL (JAX) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$164 RT
Kansas City, MO (MCI) 330 day travel period.. No min. stay. (Delta) See all details »
$164 RT
Kansas City, MO (MCI) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$138 RT
Kansas City, MO (MCI) Spring travel; Nonstop flights.. No min. stay.. Fare can be bought one-... (Southwest) See all details »
$300 RT
Knoxville, TN (TYS) 330 day travel period. (Delta) See all details »
$238 RT
Las Vegas, NV (LAS) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$284 RT
Las Vegas, NV (LAS) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$284 RT
Las Vegas, NV (LAS) Spring travel. (Delta) See all details »
$336 RT
Little Rock, AR (LIT) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$385 RT
Long Beach, CA (LGB) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$366 RT
Los Angeles, CA (LAX) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$360 RT
Los Angeles, CA (LAX) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$200 RT
Louisville, KY (SDF) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$188 RT
Louisville, KY (SDF) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$200 RT
Louisville, KY (SDF) No min. stay. (Delta) See all details »
$260 RT
Manchester, NH (MHT) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$284 RT
Manchester, NH (MHT) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$260 RT
Manchester, NH (MHT) No peak summer travel at this price. (Delta) See all details »
$286 RT
Melbourne, FL (MLB) 330 day travel period.. No min. stay. (Delta) See all details »
$245 RT
Memphis, TN (MEM) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$245 RT
Memphis, TN (MEM) No min. stay. (Delta) See all details »
$184 RT
Miami, FL (MIA) 330 day travel period.. No peak holiday travel at this price. (Delta) See all details »
$184 RT
Miami, FL (MIA) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$148 RT
Minneapolis, MN (MSP) Spring travel; Nonstop flights.. No min. stay.. Fare can be bought one-... (Southwest) See all details »
$109 RT
Minneapolis, MN (MSP) Spring travel; Nonstop flights.. No min. stay.. Fare can be bought one-... (Sun Country Airlines) See all details »
$109 RT
Minneapolis, MN (MSP) Lowest fare found for travel within the next 30 days. (Sun Country Airlines) See all details »
$236 RT
Myrtle Beach, SC (MYR) (Delta) See all details »
$256 RT
Nashville, TN (BNA) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$256 RT
Nashville, TN (BNA) 330 day travel period.. No min. stay. (Delta) See all details »
$250 RT
Nashville, TN (BNA) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$184 RT
New Orleans, LA (MSY) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$228 RT
New York City, NY (LGA) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$244 RT
New York City, NY (JFK) No min. stay.. No peak holiday travel at this price. (Delta) See all details »
$244 RT
New York City, NY (JFK) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$431 RT
New York City, NY (LGA) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$232 RT
Newark, NJ (EWR) 330 day travel period.. No peak holiday travel at this price. (Delta) See all details »
$232 RT
Newark, NJ (EWR) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$256 RT
Newark, NJ (EWR) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$306 RT
Norfolk, VA (ORF) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$390 RT
Oakland, CA (OAK) 330 day travel period.. No min. stay.. No peak holiday travel at this p... (Delta) See all details »
$410 RT
Oakland, CA (OAK) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$368 RT
Oakland, CA (OAK) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$310 RT
Oklahoma City, OK (OKC) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$235 RT
Omaha, NE (OMA) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$477 RT
Ontario, CA (ONT) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$270 RT
Orlando, FL (MCO) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$286 RT
Orlando, FL (MCO) No min. stay. (Delta) See all details »
$286 RT
Orlando, FL (MCO) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$298 RT
Pensacola, FL (PNS) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$348 RT
Philadelphia, PA (PHL) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$348 RT
Philadelphia, PA (PHL) 330 day travel period.. No min. stay. (Delta) See all details »
$298 RT
Philadelphia, PA (PHL) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$348 RT
Phoenix, AZ (PHX) 330 day travel period.. No min. stay.. No peak holiday travel at this p... (Delta) See all details »
$361 RT
Phoenix, AZ (PHX) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$372 RT
Phoenix, AZ (PHX) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$248 RT
Pittsburgh, PA (PIT) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$248 RT
Pittsburgh, PA (PIT) 330 day travel period.. No min. stay. (Delta) See all details »
$234 RT
Pittsburgh, PA (PIT) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$390 RT
Portland, OR (PDX) Late Summer/Fall/Winter travel.. No peak holiday travel at this price. (Delta) See all details »
$408 RT
Portland, OR (PDX) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$414 RT
Portland, OR (PDX) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$260 RT
Providence, RI (PVD) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$164 RT
Raleigh, NC (RDU) 330 day travel period.. No min. stay. (Delta) See all details »
$118 RT
Raleigh, NC (RDU) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$375 RT
Reno, NV (RNO) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$350 RT
Richmond, VA (RIC) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$514 RT
Sacramento, CA (SMF) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$478 RT
Sacramento, CA (SMF) No peak summer travel at this price. (Delta) See all details »
$462 RT
Sacramento, CA (SMF) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$226 RT
Salt Lake City, UT (SLC) Late Summer/Fall travel; Nonstop flights.. No min. stay.. Fare can be b... (Southwest) See all details »
$386 RT
Salt Lake City, UT (SLC) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$330 RT
San Antonio, TX (SAT) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$390 RT
San Diego, CA (SAN) 330 day travel period.. No min. stay. (Delta) See all details »
$397 RT
San Diego, CA (SAN) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$414 RT
San Diego, CA (SAN) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$286 RT
San Francisco, CA (SFO) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$286 RT
San Francisco, CA (SFO) No min. stay.. No peak summer travel at this price. (Delta) See all details »
$368 RT
San Francisco, CA (SFO) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$324 RT
San Jose, CA (SJC) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$357 RT
San Juan, Puerto Rico (SJU) Fall/Winter travel. (Delta) See all details »
$412 RT
Santa Ana, CA (SNA) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$376 RT
Santa Ana, CA (SNA) No min. stay. (Delta) See all details »
$360 RT
Santa Ana, CA (SNA) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$438 RT
Sarasota, FL (SRQ) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$342 RT
Seattle, WA (SEA) 330 day travel period.. No min. stay. (Delta) See all details »
$364 RT
Seattle, WA (SEA) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$366 RT
Seattle, WA (SEA) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$286 RT
Spokane, WA (GEG) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$236 RT
St. Louis, MO (STL) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$220 RT
St. Louis, MO (STL) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$236 RT
St. Louis, MO (STL) No min. stay. (Delta) See all details »
$184 RT
Tampa, FL (TPA) No min. stay.. No peak holiday travel at this price. (Delta) See all details »
$158 RT
Tampa, FL (TPA) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$184 RT
Tampa, FL (TPA) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$209 RT
Toronto, ON, Canada (YTZ) Lowest fare found for travel within the next 30 days. (Porter Airlines) See all details »
$446 RT
Tucson, AZ (TUS) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$296 RT
Tulsa, OK (TUL) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$342 RT
Washington, D.C. (DCA) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$342 RT
Washington, D.C. (IAD) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$326 RT
Washington, D.C. (IAD) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$326 RT
Washington, D.C. (DCA) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$346 RT
Washington, D.C. (IAD) 330 day travel period. (Delta) See all details »
$346 RT
Washington, D.C. (DCA) 330 day travel period. (Delta) See all details »
$184 RT
West Palm Beach, FL (PBI) 330 day travel period.. No peak holiday travel at this price. (Delta) See all details »
$184 RT
West Palm Beach, FL (PBI) Lowest fare found for travel within the next 30 days. (Delta) See all details »
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Low Fares to Springfield, Illinois (SPI)
Details
$177 RT
Chicago, IL (ORD) Non-Stop Flights.. No min. stay. (United) See all details »
$177 RT
Chicago, IL (ORD) Non-Stop Flights.. No min. stay. (United) See all details »
$299 RT
Orlando, FL (MCO) 330 day travel period.. No peak holiday travel at this price. (United, American) See all details »

Low Fares to Peoria, Illinois (PIA)
Details
$440 RT
Dallas, TX (DFW) Lowest fare found for travel within the next 30 days. (Delta, United) See all details »
$299 RT
Fargo, ND (FAR) 330 day travel period. (Delta, United, American) See all details »

Low Fares to Milwaukee, Wisconsin (MKE)
Details
$247 RT
Atlanta, GA (ATL) Non-Stop Flights. (Delta) See all details »
$247 RT
Atlanta, GA (ATL) Lowest fare found for travel within the next 30 days. (Delta) See all details »
$248 RT
Atlanta, GA (ATL) Non-Stop Flights.. No min. stay.. Fare can be bought one-way for half t... (Southwest) See all details »
$276 RT
Austin, TX (AUS) Late Summer/Fall travel. (American) See all details »
$282 RT
Austin, TX (AUS) Lowest fare found for travel within the next 30 days. (US Airways, American) See all details »

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Low Fares to Chicago, Illinois (ORD)
Details
$255 RT
Akron, OH (CAK) Lowest fare found for travel within the next 30 days. (United) See all details »
$344 RT
Albany, NY (ALB) Lowest fare found for travel within the next 30 days. (US Airways, American) See all details »
$367 RT
Albany, NY (ALB) Non-Stop Flights.. No peak holiday travel at this price. (United) See all details »
$408 RT
Albuquerque, NM (ABQ) Lowest fare found for travel within the next 30 days. (Delta, US Airways) See all details »
$444 RT
Allentown, PA (ABE) Lowest fare found for travel within the next 30 days. (Delta, US Airways, American) See all details »

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