Title: CA $350 Cheap Flights from Kingston (KIN) to Chicago (ORD) - Expedia.ca

  

![City of Chicago. Image of Chicago downtown and Chicago River with bridges at sunny summer day](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# CA $350 Cheap Flights from Kingston (KIN) to Chicago (ORD)

[View CA $350 flight on Tue, Dec 16, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:KIN,to:ORD,departure:16/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:349.72&airProductToken=AQpcCiwIzpYBEgQyMDUxGIpqIOVaKKvx_wIwlfL_AjhXQABYAWoCUlByBldBMjFOUgosCM6WARIEMTk4NhjlWiCuHCil9f8CMPH2_wI4V0ABWAFqAlJQcgZXQTIxTlISCggBEAEYASoCTksYASIECAEQASgCKAMoBDAN)

-   [Roundtrip](?flightType=roundtrip)
-   [One-way](?flightType=oneway)
-   [Multi-city](?flightType=multicity)

### Travellers

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## Popular airlines from Norman Manley Intl. Airport (KIN) to Chicago O'Hare International Airport (ORD)

-   ![JetBlue Airways](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg)
    
    JetBlue Airways
    
    [](https://www.expedia.ca/Flights-Search?leg1=from:kin,to:ord,departure:20/11/2025TANYT&leg2=from:ord,to:kin,departure:27/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}])
-   ![Delta](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg)
    
    Delta
    
    [](https://www.expedia.ca/Flights-Search?leg1=from:kin,to:ord,departure:20/11/2025TANYT&leg2=from:ord,to:kin,departure:27/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}])
-   ![American Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg)
    
    American Airlines
    
    [](https://www.expedia.ca/Flights-Search?leg1=from:kin,to:ord,departure:20/11/2025TANYT&leg2=from:ord,to:kin,departure:27/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}])
-   ![Copa](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_CM.svg)
    
    Copa
    
    [](https://www.expedia.ca/Flights-Search?leg1=from:kin,to:ord,departure:20/11/2025TANYT&leg2=from:ord,to:kin,departure:27/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"CM"}}])
-   ![United](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg)
    
    United
    
    [](https://www.expedia.ca/Flights-Search?leg1=from:kin,to:ord,departure:20/11/2025TANYT&leg2=from:ord,to:kin,departure:27/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}])
-   ![Air Canada](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AC.svg)
    
    Air Canada
    
    [](https://www.expedia.ca/Flights-Search?leg1=from:kin,to:ord,departure:20/11/2025TANYT&leg2=from:ord,to:kin,departure:27/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AC"}}])
-   ![Spirit Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_NK.svg)
    
    Spirit Airlines
    
    [](https://www.expedia.ca/Flights-Search?leg1=from:kin,to:ord,departure:20/11/2025TANYT&leg2=from:ord,to:kin,departure:27/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NK"}}])

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## Cheap flights from Kingston (KIN) to Chicago (ORD)

Prices were available within the past 7 days and start at CA $350 for one-way flights and CA $571 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

All deals

One way

Roundtrip

![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif)

Sun, Dec 21 - Sun, Jan 4

KIN

Kingston

ORD

Chicago

CA $571

Roundtrip

found 3 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:KIN,to:ORD,departure:21/12/2025TANYT&leg2=from:ORD,to:KIN,departure:04/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:570.44&airProductToken=AQpcCiwIzpYBEgQyMDUxGIpqIOVaKMupgAMwtaqAAzhHQABYAWoCUlByBkdBMjFOUgosCM6WARIEMTk4NhjlWiCuHCjerYADMKavgAM4R0ABWAFqAlJQcgZHQTIxTlIKWQopCM6WARIBMRiuHCDlWijUw4EDMJLFgQM4VUAAWAFqAlNEcgZVQTE0TlIKLAjOlgESBDIwNTAY5Vogimoo4MWBAzDKxoEDOFVAAVgBagJTRHIGVUExNE5SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ)

![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif)

Sun, Dec 21 - Sun, Jan 4

KIN

Kingston

ORD

Chicago

CA $635

Roundtrip

found 3 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:KIN,to:ORD,departure:21/12/2025TANYT&leg2=from:ORD,to:KIN,departure:04/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:634.67&airProductToken=AQpcCiwIzpYBEgQyMDUxGIpqIOVaKMupgAMwtaqAAzhHQABYAWoCUlByBkdBMjFOUgosCM6WARIEMTk4NhjlWiCuHCjerYADMKavgAM4R0ABWAFqAlJQcgZHQTIxTlISCggBEAEYASoCTksYASIECAEQASgCKAMoBDAN)

![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif)

Sun, Dec 21 - Sun, Jan 4

KIN

Kingston

ORD

Chicago

CA $672

Roundtrip

found 3 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:KIN,to:ORD,departure:21/12/2025TANYT&leg2=from:ORD,to:KIN,departure:04/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:671.67&airProductToken=AQpcCiwIzpYBEgQyMDUxGIpqIOVaKMupgAMwtaqAAzhHQABYAWoCUlByBkdBMjFOUgosCM6WARIEMTk4NhjlWiCuHCjerYADMKavgAM4R0ABWAFqAlJQcgZHQTIxTlISCggBEAEYASoCTksYASIECAEQASgCKAMoBDAN)

![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif)

Sun, Dec 21 - Sun, Jan 4

KIN

Kingston

ORD

Chicago

CA $837

Roundtrip

found 3 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:KIN,to:ORD,departure:21/12/2025TANYT&leg2=from:ORD,to:KIN,departure:04/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:836.23&airProductToken=AQpcCiwIzpYBEgQyMDUxGIpqIOVaKMupgAMwtaqAAzhHQABYAWoCUlByBkdBMjFOUgosCM6WARIEMTk4NhjlWiCuHCjerYADMKavgAM4R0ABWAFqAlJQcgZHQTIxTlISCggBEAEYASoCTksYASIECAEQASgCKAMoBDAN)

![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif)

Sun, Dec 21 - Sun, Jan 4

KIN

Kingston

ORD

Chicago

CA $840

Roundtrip

found 3 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:KIN,to:ORD,departure:21/12/2025TANYT&leg2=from:ORD,to:KIN,departure:04/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:839.67&airProductToken=AQpcCiwIzpYBEgQyMDUxGIpqIOVaKMupgAMwtaqAAzhHQABYAWoCUlByBkdBMjFOUgosCM6WARIEMTk4NhjlWiCuHCjerYADMKavgAM4R0ABWAFqAlJQcgZHQTIxTlISCggBEAEYASoCTksYASIECAEQASgCKAMoBDAN)

![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif)

Sun, Dec 21 - Sun, Jan 4

KIN

Kingston

ORD

Chicago

CA $851

Roundtrip

found 3 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:KIN,to:ORD,departure:21/12/2025TANYT&leg2=from:ORD,to:KIN,departure:04/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:850.65&airProductToken=AQpbCiwIzpYBEgQyMDUxGIpqIOVaKMupgAMwtaqAAzhHQABYAWoCUlByBkdBMjFOUgorCM6WARIDMzUyGOVaIK4cKICrgAMwx6yAAzhHQAFYAWoCUlByBkdBMjFOUhIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0)

![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif)

Sun, Dec 21 - Sun, Jan 4

KIN

Kingston

ORD

Chicago

CA $902

Roundtrip

found 3 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:KIN,to:ORD,departure:21/12/2025TANYT&leg2=from:ORD,to:KIN,departure:04/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:901.88&airProductToken=AQpcCiwIzpYBEgQyMDUxGIpqIOVaKMupgAMwtaqAAzhHQABYAWoCUlByBkdBMjFOUgosCM6WARIEMTk4NhjlWiCuHCjerYADMKavgAM4R0ABWAFqAlJQcgZHQTIxTlISCggBEAEYASoCTksYASIECAEQASgCKAMoBDAN)

![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif)

Sun, Dec 21 - Sun, Jan 4

KIN

Kingston

ORD

Chicago

CA $981

Roundtrip

found 3 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:KIN,to:ORD,departure:21/12/2025TANYT&leg2=from:ORD,to:KIN,departure:04/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:980.24&airProductToken=AQpeCi0IwmwSBDE3NjAYimogqVEo5KyAAzDLroADOFBAAFgBagJBTnIIUEkyUVVFWTUKLQjCbBIEMTMwNRipUSCuHCj8t4ADMLS5gAM4VkABWAFqAkFOcghWSTBBVUVZNRIKCAEQARgBKgJCNhgBIgQIARABKAIoAygEMAE)

![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif)

Sun, Dec 21 - Sun, Jan 4

KIN

Kingston

ORD

Chicago

CA $983

Roundtrip

found 3 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:KIN,to:ORD,departure:21/12/2025TANYT&leg2=from:ORD,to:KIN,departure:04/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:982.82&airProductToken=AQpeCi0IwmwSBDEwNjAYimogqVEop62AAzCSr4ADOFBAAFgBagJBTnIIUEkyUVVFWTUKLQjCbBIEMTMwNRipUSCuHCj8t4ADMLS5gAM4VkABWAFqAkFOcghWSTBBVUVZNRIKCAEQARgBKgJCNhgBIgQIARABKAIoAygEMAE)

![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif)

Sun, Dec 21 - Sun, Jan 4

KIN

Kingston

ORD

Chicago

CA $1,020

Roundtrip

found 3 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:KIN,to:ORD,departure:21/12/2025TANYT&leg2=from:ORD,to:KIN,departure:04/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1019.82&airProductToken=AQpdCiwIwmwSAzc2MBiKaiCpUSjZpYADMMCngAM4UEAAWAFqAkFOcghQSTJRVUVZNQotCMJsEgQxMzA1GKlRIK4cKNysgAMwlK6AAzhWQAFYAWoCQU5yCFZJMEFVRVk1EgoIARABGAEqAkI2GAEiBAgBEAEoAigDKAQwAQ)

## Find the cheapest month to fly from Kingston (KIN) to Chicago (ORD)

### February is typically the cheapest month to fly

From CA $366 - CA $805 per traveller.

Flight from Kingston to Chicago (KIN - ORD) route information

| Origin airport | Norman Manley Intl. |
| --- | --- |
| Destination airport | O'Hare Intl. |
| Roundtrip price | CA $570 |
| Distance | 2856 km |

## Kingston to Chicago Flights

**The easy way to book your flights from Kingston to Chicago** 

With Expedia, it’s simple to find and book flights to Chicago from Kingston whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to O'Hare Intl., 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 Kingston to Chicago today, tomorrow, or this week.  

**Save dollars with cheap flights from Norman Manley Intl., KIN to O'Hare Intl., ORD** 

Sort your search results by price to find great deals on your flight from Kingston to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Kingston currently is just CA $571 rising to CA $1,020.  

Here are more money-saving tips: 

-   Fly in December 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 Kingston** 

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.

## Frequently asked questions

### How much is a flight from Norman Manley Intl. Airport to O'Hare Intl. Airport (ORD)?

> Round-trip journeys from Norman Manley Intl. Airport (KIN) to O'Hare Airport start from CA $571. This is based on fares offered within the last 7 days on Expedia for flights departing within the next year — book now to avoid missing out. Prices and availability are subject to change. Additional terms apply.

### Do I need to pay a cancellation fee if I cancel my flight from Norman Manley Intl. Airport to ORD?

> We understand that your situation can change unexpectedly, so we've made it as hassle-free as possible for you to cancel your trip online. Just visit the [Customer Service Portal](https://www.expedia.ca/helpcenter) and follow the instructions.

### How do I find cheap flights from Norman Manley Intl. Airport (KIN) to ORD that have flexible change policies?

> Use our "No change fees" filter to find flexible ticketing options for your flight from Norman Manley Intl. Airport (KIN) to ORD. This allows you to secure a good price in advance and still have the freedom to reschedule without any additional fees. Keep in mind that you'll need to cover the fare difference.

### How many hours is the flight from Norman Manley Intl. Airport to O'Hare Intl. Airport (ORD)?

> It takes roughly 6 hours and 15 minutes to journey from Norman Manley Intl. Airport to ORD. But with some movies and an interesting book, the hours will go by quicker.

### How far is the flight from Norman Manley Intl. Airport to O'Hare Airport?

> The flight distance from Kingston to Chicago is 2,900 kilometres. Pack yourself a drink, a snack and an interesting book to read. Keep yourself busy in the air and the time will fly by.

### Which airlines fly direct from Norman Manley Intl. Airport (KIN) to O'Hare Intl. Airport (ORD)?

> Unfortunately, there are no airlines that fly directly between Norman Manley Intl. Airport and O'Hare Intl. Airport (ORD). You'll need to book a flight with at least one stop.

### Are KIN to ORD flight tickets cheaper when they're purchased at the last minute?

> It is possible to find an amazing last-minute deal from KIN to ORD, but it's also possible to miss out altogether! As many airlines publish prices up to 12 months in advance, it's worth keeping an eye on fares early and being ready to book when you spot a good bargain. Expedia compares air carrier prices and updates flight deals all the time, so you can feel confident knowing you're always seeing the latest offers.

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-   [Flights from Belize City (BZE) to Chicago (MDW)](https://www.expedia.ca/lp/flights/bze/mdw/belize-city-to-chicago)
-   [Flights from Charleston (CHS) to Chicago (MDW)](https://www.expedia.ca/lp/flights/chs/mdw/charleston-to-chicago)
-   [Flights from Cleveland (CLE) to Chicago (MDW)](https://www.expedia.ca/lp/flights/cle/mdw/cleveland-to-chicago)
-   [Flights from Danville (DAN) to Chicago (CHI)](https://www.expedia.ca/lp/flights/dan/chi/danville-to-chicago)
-   [Flights from Delhi (DEL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/del/mdw/delhi-to-chicago)
-   [Flights from Des Moines (DSM) to Chicago (MDW)](https://www.expedia.ca/lp/flights/dsm/mdw/des-moines-to-chicago)
-   [Flights from Detroit (DTW) to Chicago (MDW)](https://www.expedia.ca/lp/flights/dtw/mdw/detroit-to-chicago)
-   [Flights from Detroit (DTW) to Chicago (PWK)](https://www.expedia.ca/lp/flights/dtw/pwk/detroit-to-chicago)
-   [Flights from Exeter (EXT) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ext/chi/exeter-to-chicago)
-   [Flights from Fishers Island (FID) to Chicago (MDW)](https://www.expedia.ca/lp/flights/fid/mdw/fishers-island-to-chicago)
-   [Flights from Flint (FNT) to Waukegan (UGN)](https://www.expedia.ca/lp/flights/fnt/ugn/flint-to-waukegan)
-   [Flights from Green Bay (GRB) to Waukegan (UGN)](https://www.expedia.ca/lp/flights/grb/ugn/green-bay-to-waukegan)
-   [Flights from Grand Rapids (GRR) to Chicago (PWK)](https://www.expedia.ca/lp/flights/grr/pwk/grand-rapids-to-chicago)
-   [Flights from Gary (GYY) to Chicago (CHI)](https://www.expedia.ca/lp/flights/gyy/chi/gary-to-chicago)
-   [Flights from Niagara Falls (IAG) to Chicago (CHI)](https://www.expedia.ca/lp/flights/iag/chi/niagara-falls-to-chicago)
-   [Flights from Niagara Falls (IAG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/iag/mdw/niagara-falls-to-chicago)
-   [Flights from Wilmington (ILM) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ilm/chi/wilmington-to-chicago)
-   [Flights from Indianapolis (IND) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ind/chi/indianapolis-to-chicago)
-   [Flights from Nakhon Phanom (KOP) to Chicago (MDW)](https://www.expedia.ca/lp/flights/kop/mdw/nakhon-phanom-to-chicago)
-   [Flights from Las Vegas (LAS) to Chicago (MDW)](https://www.expedia.ca/lp/flights/las/mdw/las-vegas-to-chicago)
-   [Flights from Los Angeles (LAX) to Chicago (CHI)](https://www.expedia.ca/lp/flights/lax/chi/los-angeles-to-chicago)
-   [Flights from Montego Bay (MBJ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/mbj/mdw/montego-bay-to-chicago)
-   [Flights from Orlando (MCO) to Chicago (MDW)](https://www.expedia.ca/lp/flights/mco/mdw/orlando-to-chicago)
-   [Flights from Michigan City (MGC) to Chicago (MDW)](https://www.expedia.ca/lp/flights/mgc/mdw/michigan-city-to-chicago)
-   [Flights from Muscle Shoals (MSL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/msl/mdw/muscle-shoals-to-chicago)
-   [Flights from Minneapolis (MSP) to Chicago (CHI)](https://www.expedia.ca/lp/flights/msp/chi/minneapolis-to-chicago)
-   [Flights from New York (NYC) to Chicago (CHI)](https://www.expedia.ca/lp/flights/nyc/chi/new-york-to-chicago)
-   [Flights from Omaha (OMA) to Chicago (MDW)](https://www.expedia.ca/lp/flights/oma/mdw/omaha-to-chicago)
-   [Flights from Chicago (ORD) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ord/chi/chicago-to-chicago)
-   [Flights from Philadelphia (PHL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/phl/mdw/philadelphia-to-chicago)
-   [Flights from Pueblo (PUB) to Chicago (MDW)](https://www.expedia.ca/lp/flights/pub/mdw/pueblo-to-chicago)
-   [Flights from Punta Cana (PUJ) to Chicago (CHI)](https://www.expedia.ca/lp/flights/puj/chi/punta-cana-to-chicago)
-   [Flights from Roanoke (ROA) to Chicago (MDW)](https://www.expedia.ca/lp/flights/roa/mdw/roanoke-to-chicago)
-   [Flights from Selinsgrove (SEG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/seg/mdw/selinsgrove-to-chicago)
-   [Flights from Sacramento (SMF) to Chicago (MDW)](https://www.expedia.ca/lp/flights/smf/mdw/sacramento-to-chicago)
-   [Flights from St. Louis (STL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/stl/mdw/st-louis-to-chicago)
-   [Flights from Newburgh (SWF) to Chicago (MDW)](https://www.expedia.ca/lp/flights/swf/mdw/newburgh-to-chicago)
-   [Flights from Sydney (SYD) to Chicago (MDW)](https://www.expedia.ca/lp/flights/syd/mdw/sydney-to-chicago)
-   [Flights from Syracuse (SYR) to Chicago (MDW)](https://www.expedia.ca/lp/flights/syr/mdw/syracuse-to-chicago)
-   [Flights from Fort Leonard Wood (TBN) to Chicago (MDW)](https://www.expedia.ca/lp/flights/tbn/mdw/fort-leonard-wood-to-chicago)
-   [Flights from Ua Pou (UAP) to Chicago (CHI)](https://www.expedia.ca/lp/flights/uap/chi/ua-pou-to-chicago)
-   [Flights from Fort Frances (YAG) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yag/chi/fort-frances-to-chicago)
-   [Flights from Brandon (YBR) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ybr/mdw/brandon-to-chicago)
-   [Flights from Nanaimo (YCD) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ycd/chi/nanaimo-to-chicago)
-   [Flights from St. Catharines (YCM) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ycm/chi/st-catharines-to-chicago)
-   [Flights from Edmonton (YEA) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yea/chi/edmonton-to-chicago)
-   [Flights from Edmonton (YEG) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yeg/chi/edmonton-to-chicago)
-   [Flights from Edmonton (YEG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yeg/mdw/edmonton-to-chicago)
-   [Flights from Flin Flon (YFO) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yfo/chi/flin-flon-to-chicago)
-   [Flights from Hamilton (YHM) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yhm/mdw/hamilton-to-chicago)
-   [Flights from Kamloops (YKA) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yka/chi/kamloops-to-chicago)
-   [Flights from Kelowna (YLW) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ylw/mdw/kelowna-to-chicago)
-   [Flights from Montreal (YMQ) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ymq/chi/montreal-to-chicago)
-   [Flights from Ottawa (YOW) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yow/mdw/ottawa-to-chicago)
-   [Flights from Peterborough (YPQ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ypq/mdw/peterborough-to-chicago)
-   [Flights from Québec (YQB) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yqb/mdw/quebec-to-chicago)
-   [Flights from Regina (YQR) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yqr/chi/regina-to-chicago)
-   [Flights from Regina (YQR) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yqr/mdw/regina-to-chicago)
-   [Flights from Gander (YQX) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yqx/chi/gander-to-chicago)
-   [Flights from Sudbury (YSB) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ysb/mdw/sudbury-to-chicago)
-   [Flights from Timmins (YTS) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yts/mdw/timmins-to-chicago)
-   [Flights from Toronto (YTZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ytz/mdw/toronto-to-chicago)
-   [Flights from Montreal (YUL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yul/mdw/montreal-to-chicago)
-   [Flights from Winnipeg (YWG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ywg/mdw/winnipeg-to-chicago)
-   [Flights from Winnipeg (YWG) to Chicago (PWK)](https://www.expedia.ca/lp/flights/ywg/pwk/winnipeg-to-chicago)
-   [Flights from Whitehorse (YXY) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yxy/chi/whitehorse-to-chicago)
-   [Flights from Calgary (YYC) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yyc/mdw/calgary-to-chicago)
-   [Flights from Victoria (YYJ) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yyj/chi/victoria-to-chicago)
-   [Flights from St. John's (YYT) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yyt/chi/st-johns-to-chicago)
-   [Flights from Toronto (YYZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yyz/mdw/toronto-to-chicago)
-   [Flights from Toronto (YYZ) to Chicago (PWK)](https://www.expedia.ca/lp/flights/yyz/pwk/toronto-to-chicago)

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