Title: CA $287 Cheap Flights from San José del Cabo (SJD) to Chicago (ORD) - Expedia.ca

  

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# CA $287 Cheap Flights from San José del Cabo (SJD) to Chicago (ORD)

[View CA $287 flight on Tue, Feb 10, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:SJD,to:ORD,departure:10/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:286.34&airProductToken=AQpeCi0I2WgSBDExNDUYshog5lgo3-eEAzC66IQDOExAAFgBagRaZXJvcgZMTENTUzIKLQjZaBIEMTcwMhjmWCCuHCif6oQDMI3shAM4TEABWAFqBFplcm9yBkxMQ1NTMhIKCAEQARgBKgJZNBgBIgQIARABKAIoAygEMA0)

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

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## Popular airlines from Los Cabos Intl. Airport (SJD) to Chicago O'Hare International Airport (ORD)

-   ![Alaska Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg)
    
    Alaska Airlines
    
    [](https://www.expedia.ca/Flights-Search?leg1=from:sjd,to:ord,departure:24/10/2025TANYT&leg2=from:ord,to:sjd,departure:31/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}])
-   ![Aeromexico](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AM.svg)
    
    Aeromexico
    
    [](https://www.expedia.ca/Flights-Search?leg1=from:sjd,to:ord,departure:24/10/2025TANYT&leg2=from:ord,to:sjd,departure:31/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AM"}}])
-   ![Volaris](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_Y4.svg)
    
    Volaris
    
    [](https://www.expedia.ca/Flights-Search?leg1=from:sjd,to:ord,departure:24/10/2025TANYT&leg2=from:ord,to:sjd,departure:31/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"Y4"}}])
-   ![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:sjd,to:ord,departure:24/10/2025TANYT&leg2=from:ord,to:sjd,departure:31/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}])
-   ![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:sjd,to:ord,departure:24/10/2025TANYT&leg2=from:ord,to:sjd,departure:31/10/2025TANYT&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:sjd,to:ord,departure:24/10/2025TANYT&leg2=from:ord,to:sjd,departure:31/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}])
-   ![Viva Aerobus](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_VB.svg)
    
    Viva Aerobus
    
    [](https://www.expedia.ca/Flights-Search?leg1=from:sjd,to:ord,departure:24/10/2025TANYT&leg2=from:ord,to:sjd,departure:31/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"VB"}}])

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## Cheap flights from San José del Cabo (SJD) to Chicago (ORD)

Prices were available within the past 7 days and start at CA $287 for one-way flights and CA $512 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

All deals

One way

Roundtrip

![Volaris](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/Y4.gif)

Fri, Apr 17 - Wed, Apr 22

SJD

San José del Cabo

ORD

Chicago

CA $512

Roundtrip

found 3 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJD,to:ORD,departure:17/04/2026TANYT&leg2=from:ORD,to:SJD,departure:22/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:511.62&airProductToken=AQpeCi0I2WgSAzMwMxiyGiCMuQEo382KAzDfzooDOExAAFgBagRaZXJvcgZMTENTUzIKLQjZaBIDNzAyGIy5ASCuHCjK0IoDMLfSigM4TEABWAFqBFplcm9yBkxMQ1NTMgpeCi0I2WgSAzcwMRiuHCCMuQEop4OLAzCthYsDOExAAFgBagRaZXJvcgZMTENTUzEKLQjZaBIDMzAwGIy5ASCyGijhhosDMOqHiwM4TEABWAFqBFplcm9yBkxMQ1NTMRIKCAEQARgBKgJZNBgBIgQIARABKAIoAygEMA0)

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

Fri, Apr 17 - Wed, Apr 22

SJD

San José del Cabo

ORD

Chicago

CA $543

Roundtrip

found 3 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJD,to:ORD,departure:17/04/2026TANYT&leg2=from:ORD,to:SJD,departure:22/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:542.45&airProductToken=AQptCjUI1oQBEgQ0MzI1GLIaIOzEASjMzIoDMLXNigM4WkAAWAFqCVZJVkFMSUdIVHIHWkxTTzAwTgo0CNaEARIDNjMyGOzEASCuHCjW0YoDMJnTigM4WkAAWAFqCVZJVkFMSUdIVHIHWkxTTzAwSRIKCAsQARgIKgJWQhgBIgQIARABKAIwAw)

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

Fri, Apr 17 - Wed, Apr 22

SJD

San José del Cabo

ORD

Chicago

CA $562

Roundtrip

found 3 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJD,to:ORD,departure:17/04/2026TANYT&leg2=from:ORD,to:SJD,departure:22/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:561.96&airProductToken=AQprCjQI1oQBEgQzMTU1GLIaIOZYKNXOigMwtM-KAzhBQABYAWoJVklWQUxJR0hUcgdBTFNPMDBOCjMI1oQBEgM1NDYY5lggrhwo8tCKAzDd0ooDOFpAAFgBaglWSVZBTElHSFRyB1pMU08wMEkSCggLEAEYCCoCVkIYASIECAEQASgCMAM)

![Volaris](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/Y4.gif)

Fri, Apr 17 - Wed, Apr 22

SJD

San José del Cabo

ORD

Chicago

CA $595

Roundtrip

found 3 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJD,to:ORD,departure:17/04/2026TANYT&leg2=from:ORD,to:SJD,departure:22/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:594.30&airProductToken=AQpeCi0I2WgSAzMwMRiyGiCMuQEo78-KAzDt0IoDOExAAFgBagRaZXJvcgZMTENTUzIKLQjZaBIDNzAwGIy5ASCuHCjQ04oDML3VigM4TEABWAFqBFplcm9yBkxMQ1NTMhIKCAEQARgBKgJZNBgBIgQIARABKAIoAygEMA0)

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

Fri, Apr 17 - Wed, Apr 22

SJD

San José del Cabo

ORD

Chicago

CA $603

Roundtrip

found 3 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJD,to:ORD,departure:17/04/2026TANYT&leg2=from:ORD,to:SJD,departure:22/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:602.70&airProductToken=AQptCjUI1oQBEgQxMjEzGLIaIIy5ASj00YoDMPHSigM4V0AAWAFqCVZJVkFMSUdIVHIHV0xTTzAwTgo0CNaEARIDMTg2GIy5ASCuHCiB1ooDMPbXigM4WkAAWAFqCVZJVkFMSUdIVHIHWkxTTzAwSRIKCAsQARgIKgJWQhgBIgQIARABKAIwAw)

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

Fri, Apr 17 - Wed, Apr 22

SJD

San José del Cabo

ORD

Chicago

CA $615

Roundtrip

found 3 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJD,to:ORD,departure:17/04/2026TANYT&leg2=from:ORD,to:SJD,departure:22/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:614.19&airProductToken=AQprCjQI1oQBEgQzMTU1GLIaIOZYKNXOigMwtM-KAzhBQABYAWoJVklWQUxJR0hUcgdBTFNPMDBOCjMI1oQBEgM1NDQY5lggrhwo4dmKAzDb24oDOENAAFgBaglWSVZBTElHSFRyB0NMU08wMEkSCggLEAEYCCoCVkIYASIECAEQASgCMAM)

![Volaris](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/Y4.gif)

Fri, Apr 17 - Wed, Apr 22

SJD

San José del Cabo

ORD

Chicago

CA $635

Roundtrip

found 3 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJD,to:ORD,departure:17/04/2026TANYT&leg2=from:ORD,to:SJD,departure:22/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:634.20&airProductToken=AQpeCi0I2WgSAzMwMRiyGiCMuQEo78-KAzDt0IoDOExAAFgBagRaZXJvcgZMTENTUzIKLQjZaBIDNzAwGIy5ASCuHCjQ04oDML3VigM4TEABWAFqBFplcm9yBkxMQ1NTMhIKCAEQARgBKgJZNBgBIgQIARABKAIoAygEMA0)

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

Fri, Apr 17 - Wed, Apr 22

SJD

San José del Cabo

ORD

Chicago

CA $647

Roundtrip

found 3 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJD,to:ORD,departure:17/04/2026TANYT&leg2=from:ORD,to:SJD,departure:22/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:646.08&airProductToken=AQozCjEIwYIBEgQyNjM2GLIaIK4cKMHOigMwwNCKAzhCQABYAWoFQkFTSUNyCE9OVTJBREJaEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw)

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

Fri, Apr 17 - Wed, Apr 22

SJD

San José del Cabo

ORD

Chicago

CA $727

Roundtrip

found 3 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJD,to:ORD,departure:17/04/2026TANYT&leg2=from:ORD,to:SJD,departure:22/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:726.68&airProductToken=AQpgCi4IwaYBEgQxMzk1GLIaIJJoKNDOigMw3M-KAzhPQABYAWoCTUFyCE9IMk9DSk1OCi4IwaYBEgQxNDkzGJJoIK4cKMDQigMwutKKAzhPQAFYAWoCTUFyCE9IMk9DSk1OEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ)

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

Fri, Apr 17 - Wed, Apr 22

SJD

San José del Cabo

ORD

Chicago

CA $789

Roundtrip

found 3 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SJD,to:ORD,departure:17/04/2026TANYT&leg2=from:ORD,to:SJD,departure:22/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:788.48&airProductToken=AQpuCjUIxJgBEgQxODQ4GLIaIOBcKKPOigMwj9CKAzhFQABYAWoJTUFJTkJBU0lDcghYTlhMME5CTQo1CMSYARIEMTE5ORjgXCCuHCjl0YoDMOfSigM4RUABWAFqCU1BSU5CQVNJQ3IIWE5YTDBOQk0Kbgo1CMSYARIEMTI2NBiuHCDgXCjUgosDMM6DiwM4RUAAWAFqCU1BSU5CQVNJQ3IIWE5YTDBOQk0KNQjEmAESBDE5NDUY4Fwgshoo3YSLAzDihosDOEVAAVgBaglNQUlOQkFTSUNyCFhOWEwwTkJNEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ)

## Find the cheapest month to fly from San José del Cabo (SJD) to Chicago (ORD)

### August is typically the cheapest month to fly

From CA $427 - CA $761 per traveller.

Flight from San José del Cabo to Chicago (SJD - ORD) route information

| Origin airport | Los Cabos Intl. |
| --- | --- |
| Destination airport | O'Hare Intl. |
| Roundtrip price | CA $512 |
| Distance | 2890 km |
| Average flight time | 6 hours 19 mins |

## San José del Cabo to Chicago Flights

**The easy way to book your flights from San José del Cabo to Chicago** 

With Expedia, it’s simple to find and book flights to Chicago from San José del Cabo 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 American Airlines, Emirates, United Airlines 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 San José del Cabo to Chicago today, tomorrow, or this week.  

**Save dollars with cheap flights from Los Cabos Intl., SJD to O'Hare Intl., ORD** 

Sort your search results by price to find great deals on your flight from San José del Cabo to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from San José del Cabo currently is just CA $512 rising to CA $789.  

Here are more money-saving tips: 

-   Fly in April 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 San José del Cabo** 

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 SJD to ORD?

> The lowest price advertised for a round-trip flight between SJD and O'Hare Intl. Airport (ORD) is CA $512. But you better get a move on. This price is based on fares available within the last 7 days on Expedia for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

### Do I need to pay a cancellation fee if I cancel my flight from Los Cabos Airport to O'Hare Intl. Airport (ORD)?

> Each air carrier has different terms and conditions. If you decide to cancel your escape, head to our [Customer Service Portal](https://www.expedia.ca/helpcenter).

### How do I find cheap flights from SJD to O'Hare Airport that have flexible change policies?

> Many carriers offer the option to move your flight without charging a fee. All you pay is the difference in the ticket price. When searching for Los Cabos Intl. Airport (SJD) to O'Hare Airport flights, you'll see a "No change fees" box for you to pick.

### How many hours is the flight from Los Cabos Airport to ORD?

> The flight time between SJD and O'Hare Intl. Airport (ORD) is 6 hours and 39 minutes. If you get peckish on longer flights, pack some healthy snacks in your carry-on baggage.

### How far is the flight from Los Cabos Intl. Airport (SJD) to ORD?

> The flying distance from SJD to ORD is 2,900 kilometres. Listen to your favourite tunes or finish off your latest read and the trip will zip on by.

### Which airlines fly direct from Los Cabos Airport to ORD?

> There are several airlines that travel directly from Los Cabos Airport to ORD. American Airlines (AA) is a great choice, offering 30 flights on this route each month. Offering 30 flights every month along this route, United Airlines (UA) is another good option.

### Are Los Cabos Airport to O'Hare Airport flight tickets cheaper when they're purchased at the last minute?

> Flight tickets from Los Cabos Airport to O'Hare Intl. Airport (ORD) are available up to a year prior to departure on Expedia. And although you may nab a great last-minute deal, it's never a sure thing. Also, booking your flights well in advance means you'll have more choices — and you can avoid landing the dreaded middle seat! We frequently update our fares to bring you the best bargains, so keep checking in for all the latest specials.

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-   [Flights from Buffalo (BUF) to Chicago (CHI)](https://www.expedia.ca/lp/flights/buf/chi/buffalo-to-chicago)
-   [Flights from Buffalo (BUF) to Chicago (MDW)](https://www.expedia.ca/lp/flights/buf/mdw/buffalo-to-chicago)
-   [Flights from Baltimore (BWI) to Chicago (MDW)](https://www.expedia.ca/lp/flights/bwi/mdw/baltimore-to-chicago)
-   [Flights from Blaine (BWS) to Chicago (CHI)](https://www.expedia.ca/lp/flights/bws/chi/blaine-to-chicago)
-   [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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