--- title: "Cheap Flights from St. Marys (KSM) to Chicago (CHI)" description: "Cheap Flights from St. Marys (KSM) to Chicago (CHI) start at for one-way and for round trip. Earn your airline miles on top of our rewards!" canonical: "https://www.expedia.ca/lp/flights/ksm/chi/st-marys-to-chicago" language: en-CA market: CA currency: CAD prices_as_of: 2026-11-14T10:52:27Z --- # Cheap Flights from St. Marys (KSM) to Chicago (CHI) ![A river with a yellow boat, surrounded by tall buildings and a bridge.](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ## Popular airlines from St. Marys, AK (KSM) to Chicago [Air Canada](https://www.expedia.ca/Flights-Search?leg1=from:KSM,to:CHI,departure:28/11/2026TANYT&leg2=from:CHI,to:KSM,departure:05/12/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AC"}}]) [WestJet](https://www.expedia.ca/Flights-Search?leg1=from:KSM,to:CHI,departure:28/11/2026TANYT&leg2=from:CHI,to:KSM,departure:05/12/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WS"}}]) [Flair Airlines](https://www.expedia.ca/Flights-Search?leg1=from:KSM,to:CHI,departure:28/11/2026TANYT&leg2=from:CHI,to:KSM,departure:05/12/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F8"}}]) [American Airlines](https://www.expedia.ca/Flights-Search?leg1=from:KSM,to:CHI,departure:28/11/2026TANYT&leg2=from:CHI,to:KSM,departure:05/12/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) [United](https://www.expedia.ca/Flights-Search?leg1=from:KSM,to:CHI,departure:28/11/2026TANYT&leg2=from:CHI,to:KSM,departure:05/12/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) [Delta](https://www.expedia.ca/Flights-Search?leg1=from:KSM,to:CHI,departure:28/11/2026TANYT&leg2=from:CHI,to:KSM,departure:05/12/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) [Porter Airlines](https://www.expedia.ca/Flights-Search?leg1=from:KSM,to:CHI,departure:28/11/2026TANYT&leg2=from:CHI,to:KSM,departure:05/12/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"PD"}}]) ### Be in the know Get alerts if flight prices drop or rise\* ### Book smarter Save up to 30% on select hotels after you book a flight\* ### Earn twice Earn your airline miles on top of our rewards [Sign in](https://www.expedia.ca/login) ## Alternative airports near Chicago Prices were available within the past 7 days. Prices and availability are subject to change. [Select flight to O'Hare Intl. ORD. Average driving time to city centre is 23 minutes.](https://www.expedia.ca/Flights-Search?leg1=from:KSM,to:ORD,departure:28/11/2026TANYT&trip=oneway&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) O'H · are Intl. · 23 min · Search flights [Select flight to General Mitchell Intl. MKE. Average driving time to city centre is 1 hour 32 minutes.](https://www.expedia.ca/Flights-Search?leg1=from:KSM,to:MKE,departure:28/11/2026TANYT&trip=oneway&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) 1 h 32 min · Search flights [Select flight to Midway Intl. MDW. Closest option available. Average driving time to city centre is 16 minutes.](https://www.expedia.ca/Flights-Search?leg1=from:KSM,to:MDW,departure:28/11/2026TANYT&trip=oneway&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) 16 min · Search flights [Select flight to Dane County Regional MSN. Average driving time to city centre is 2 hours 30 minutes.](https://www.expedia.ca/Flights-Search?leg1=from:KSM,to:MSN,departure:28/11/2026TANYT&trip=oneway&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) 2 h 30 min · Search flights [Select flight to Quad City Intl. MLI. Average driving time to city centre is 2 hours 56 minutes.](https://www.expedia.ca/Flights-Search?leg1=from:KSM,to:MLI,departure:28/11/2026TANYT&trip=oneway&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) 2 h 56 min · Search flights [Select flight to Greater Rockford RFD. Average driving time to city centre is 1 hour 30 minutes.](https://www.expedia.ca/Flights-Search?leg1=from:KSM,to:RFD,departure:28/11/2026TANYT&trip=oneway&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) 1 h 30 min · Search flights [Select flight to Dubuque Regional DBQ. Average driving time to city centre is 3 hours 27 minutes.](https://www.expedia.ca/Flights-Search?leg1=from:KSM,to:DBQ,departure:28/11/2026TANYT&trip=oneway&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) 3 h 27 min · Search flights ## Book with confidence ### St. Mary's to Chicago Flights #### The easy way to book your flights from St. Marys to Chicago With Expedia, it’s simple to find and book flights to Chicago from St. Marys whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from airlines that cover this route. There are nonstop flights to CHI-All Airports, too. Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from St. Marys to Chicago today, tomorrow, or this week. #### Save dollars with cheap flights from St. Marys, AK, KSM to CHI-All Airports, CHI Sort your search results by price to find great deals on your flight from St. Marys to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from St. Marys currently is just rising to . Here are more money-saving tips: - Fly in when flight prices are normally at their lowest - Book about a month to 6 weeks before you travel for the best prices to Chicago - Avoid peak season and weekends when flights can cost more - Early morning and late-night flights are sometimes cheaper, so try varying your travel times - One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! #### Reasons to choose Expedia for your flight to Chicago from St. Marys Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today. ## Travel information | Origin airport | St. Marys, AK | | ------------------- | ---------------------- | | Destination airport | Chicago Midway Airport | | Distance | 5,276 km away | ## Explore a world of travel with Expedia - [Flights](?equalTargetTab=tab-0) - [Flights from Poughkeepsie (POU) to Chicago (CHI)](https://www.expedia.ca/lp/flights/pou/chi/poughkeepsie-to-chicago) - [Flights from Blaine (BWS) to Chicago (CHI)](https://www.expedia.ca/lp/flights/bws/chi/blaine-to-chicago) - [Flights from Laval (LVA) to Chicago (CHI)](https://www.expedia.ca/lp/flights/lva/chi/laval-to-chicago) - [Flights from Rome (RME) to Chicago (CHI)](https://www.expedia.ca/lp/flights/rme/chi/rome-to-chicago) - [Flights from Gander (YQX) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yqx/chi/gander-to-chicago) - [Flights from Winnipeg (YWG) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ywg/chi/winnipeg-to-chicago) - [Flights from Santo Domingo (SDQ) to Chicago (CHI)](https://www.expedia.ca/lp/flights/sdq/chi/santo-domingo-to-chicago) - [Flights from Winnipeg (YWG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ywg/ord/winnipeg-to-chicago) - [Flights from Halifax (YHZ) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yhz/chi/halifax-to-chicago) - [Flights from Vancouver (YVR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yvr/ord/vancouver-to-chicago) - [Flights from Cincinnati (CVG) to Chicago (CHI)](https://www.expedia.ca/lp/flights/cvg/chi/cincinnati-to-chicago) - [Flights from St. Catharines (YCM) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ycm/chi/st-catharines-to-chicago) - [Flights from Burlington (BTV) to Chicago (CHI)](https://www.expedia.ca/lp/flights/btv/chi/burlington-to-chicago) - [Flights from Montreal (YUL) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yul/ord/montreal-to-chicago) - [Flights from Gary (GYY) to Chicago (CHI)](https://www.expedia.ca/lp/flights/gyy/chi/gary-to-chicago) - [Flights from Hyderabad (HYD) to Chicago (CHI)](https://www.expedia.ca/lp/flights/hyd/chi/hyderabad-to-chicago) - [Flights from Windsor (YQG) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yqg/chi/windsor-to-chicago) - [Flights from Presque Isle (PQI) to Chicago (CHI)](https://www.expedia.ca/lp/flights/pqi/chi/presque-isle-to-chicago) - [Flights from Ottawa (YOW) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yow/chi/ottawa-to-chicago) - [Flights from Toronto (YTO) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yto/chi/toronto-to-chicago) - [Flights from Regina (YQR) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yqr/chi/regina-to-chicago) - [Flights from Fort Frances (YAG) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yag/chi/fort-frances-to-chicago) - [Flights from Cambridge (CGE) to Chicago (CHI)](https://www.expedia.ca/lp/flights/cge/chi/cambridge-to-chicago) - [Flights from Oshawa (YOO) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yoo/chi/oshawa-to-chicago) - [Flights from Traverse City (TVC) to Chicago (CHI)](https://www.expedia.ca/lp/flights/tvc/chi/traverse-city-to-chicago) - [Flights from Calgary (YYC) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyc/ord/calgary-to-chicago) - [Flights from Whitehorse (YXY) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yxy/chi/whitehorse-to-chicago) - [Flights from Newark Liberty Intl. 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[Flights from Wilmington (ILM) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ilm/chi/wilmington-to-chicago) - [Flights from Detroit (DTW) to Chicago (CHI)](https://www.expedia.ca/lp/flights/dtw/chi/detroit-to-chicago) - [Flights from San Diego (SAN) to Chicago (CHI)](https://www.expedia.ca/lp/flights/san/chi/san-diego-to-chicago) - [Flights from Owen Sound (YOS) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yos/chi/owen-sound-to-chicago) - [Flights from New Orleans (MSY) to Chicago (CHI)](https://www.expedia.ca/lp/flights/msy/chi/new-orleans-to-chicago) - [Flights from Prince Albert (YPA) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ypa/chi/prince-albert-to-chicago) - [Flights from Trois-Rivieres (YRQ) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yrq/chi/trois-rivieres-to-chicago) - [Flights from Beirut (BEY) to Chicago (CHI)](https://www.expedia.ca/lp/flights/bey/chi/beirut-to-chicago) - [Flights from Calgary (YYC) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yyc/chi/calgary-to-chicago) \*Available to Expedia members. ## Other language versions ```yaml hreflang: x-default: https://www.expedia.com/ en-CA: https://www.expedia.ca/lp/flights/ksm/chi/st-marys-to-chicago id-ID: https://www.expedia.co.id/lp/flights/ksm/chi/st-marys-to-semua-bandara-chicago ar: https://www.expedia.sa/lp/flights/ksm/chi/st-marys-to-chicago es: https://www.expedia.com/es/lp/vuelos/ksm/chi/st-marys-a-todos-los-aeropuertos-de-chicago en-PH: https://www.expedia.com.ph/lp/flights/ksm/chi/st-marys-to-chicago es-MX: https://www.expedia.mx/lp/vuelos/ksm/chi/st-marys-a-todos-los-aeropuertos-de-chicago en-JP: https://www.expedia.co.jp/en/lp/flights/ksm/chi/st-marys-to-chicago ```