Popular airlines from Hartford - Brainard Airport (HFD) to Chicago Midway Airport (MDW)
American AirlinesAmerican Airlines
UnitedUnited
Southwest AirlinesSouthwest Airlines
DeltaDelta
Frontier AirlinesFrontier Airlines
JetBlue AirwaysJetBlue Airways
Alaska AirlinesAlaska Airlines
Today's featured flight deals from Hartford - Brainard Airport (HFD) to Chicago Midway Airport (MDW)
- Hartford (BDL) to Chicago (MDW).Southwest Airlines, nonstop.Departing on Thu, Nov 13 at 5:15am from Hartford, arriving at 6:45am in Chicago.Returning on Sun, Nov 16 at 6:00am from Chicago, arriving at 2:00pm in Hartford.Select Southwest Airlines flight departing on Thu, Nov 13 at 5:15am from Hartford, returning on Sun, Nov 16 at 6:00am from Chicago priced at $17760% less than typical$177
- Hartford (BDL) to Chicago (MDW).Southwest Airlines, nonstop.Departing on Sun, Nov 2 at 5:15am from Hartford, arriving at 6:45am in Chicago.Returning on Thu, Nov 6 at 4:10pm from Chicago, arriving at 11:55pm in Hartford.Select Southwest Airlines flight departing on Sun, Nov 2 at 5:15am from Hartford, returning on Thu, Nov 6 at 4:10pm from Chicago priced at $21255% less than typical$212
- Hartford (BDL) to Chicago (MDW).Southwest Airlines, nonstop.Departing on Sat, Nov 22 at 8:05pm from Hartford, arriving at 9:35pm in Chicago.Returning on Thu, Nov 27 at 5:34pm from Chicago, arriving at 11:48pm in Hartford.Select Southwest Airlines flight departing on Sat, Nov 22 at 8:05pm from Hartford, returning on Thu, Nov 27 at 5:34pm from Chicago priced at $24545% less than typical$245
- Hartford (BDL) to Chicago (MDW).Southwest Airlines, nonstop.Departing on Thu, Nov 13 at 5:15am from Hartford, arriving at 6:45am in Chicago.Returning on Mon, Nov 17 at 5:55am from Chicago, arriving at 11:34am in Hartford.Select Southwest Airlines flight departing on Thu, Nov 13 at 5:15am from Hartford, returning on Mon, Nov 17 at 5:55am from Chicago priced at $24045% less than typical$240
- Hartford (BDL) to Chicago (MDW).Southwest Airlines, nonstop.Departing on Tue, Nov 18 at 5:40pm from Hartford, arriving at 7:10pm in Chicago.Returning on Sun, Nov 23 at 5:15pm from Chicago, arriving at 11:40pm in Hartford.Select Southwest Airlines flight departing on Tue, Nov 18 at 5:40pm from Hartford, returning on Sun, Nov 23 at 5:15pm from Chicago priced at $29535% less than typical$295
Alternative airports near Chicago
Prices were available within the past 7 days. Prices and availability are subject to change.
Travel information
Origin airport | Hartford - Brainard |
|---|---|
Destination airport | Midway Intl. |
Distance | 776 mi |
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Hartford to Chicago Flights
The cheapest times to fly from Hartford to Chicago
On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Hartford to Chicago are during the month of . You can find some of the cheapest flights from Hartford to Chicago with Expedia's search tool and vast selection of airlines.
The best time to book a flight from Hartford to Chicago
Sunday is one of the best days to book for cheap flights from Hartford to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.
How to find cheap round-trip tickets from Hartford to Chicago
Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Hartford to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.
Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Hartford to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.
You could also save big by booking one of Expedia's vacation packages. Bundling together your Hartford to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.
*Terms apply.
Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.