Cheap flights from Hartford to Chicago from $65
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Hartford to Chicago departing on 10/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Southwest flights from Hartford to Chicago Midway Airport
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Frontier flights from Hartford to Chicago Midway Airport
Our best Frontier deals on Hartford to Chicago Midway Airport flight tickets
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How to get the cheapest flight ticket from Hartford to Chicago Midway Airport
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Chicago Midway Airport?
The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from Hartford, with most prices found around $326. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Hartford during the month August is also very affordable. Most momondo users find prices during this month for around $331.
What is the cheapest Hartford Bradley Intl to Chicago Midway flight route?
Fly from Hartford Bradley Intl to Chicago Midway for the best Hartford Bradley Intl - Chicago Midway flight prices
How far in advance should I book a flight to Chicago Midway Airport?
You are more likely to see cheaper flights to Chicago Midway Airport from Hartford when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $369 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Hartford for as low as $234 on momondo.
What cabin class options are available on Hartford Bradley Intl to Chicago Midway flights?
There are 1 cabin classes available to choose from on Hartford Bradley Intl to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Hartford to Chicago Midway Airport flights?
No. A direct flight is the cheapest option for a flight between Hartford to Chicago Midway Airport.
How have Hartford to Chicago Midway Airport flight prices changed over time?
What is the cheapest airline that flies from Hartford Bradley Intl to Chicago Midway?
Frontier, Southwest, and Delta are the most popular carriers operating from Hartford Bradley Intl to Chicago Midway
What airlines fly to Chicago Midway Airport?
Southwest, Avelo Airlines and American Airlines are the top three most popular airlines that fly to Chicago Midway Airport from Hartford according to our data. Southwest is the first choice among our users, with 84% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 3 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Hartford to Chicago Midway Airport on average per day?
As of June 2025, there are 1 flights per day flying from Hartford to Chicago Midway Airport. The most common time of day flights depart is 7:00AM, with 46% of flights taking off in the afternoon.
How many flights depart from Hartford to Chicago Midway Airport on average per week?
As of June 2025, 13 flights take off from Hartford and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 23% of weekly flights taking off on this day.
When to book flights from Hartford to Chicago Midway Airport
Cheap Hartford to Chicago Midway Airport (BDL to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Hartford to Chicago Midway Airport
How far is Hartford Bradley Intl to Chicago Midway by plane?
A flight from Hartford Bradley Intl to Chicago Midway will travel around 774.9 mi. 2h 20m is a normal flight duration for this route.
When did momondo last update prices for flights from Hartford Bradley Intl Airport to Chicago Midway Airport?
Prices for flights from Hartford Bradley Intl Airport to Chicago Midway Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Hartford Bradley Intl Airport to Chicago Midway Airport?
As of June 2025, there are 4 operators available to choose from for flights from Hartford Bradley Intl Airport to Chicago Midway Airport.
How old do you have to be to fly from Hartford Bradley Intl Airport to Chicago Midway Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Hartford Bradley Intl Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Hartford to Chicago Midway Airport?
momondo data reveals that the most frequently booked plane model on the route from Hartford to Chicago Midway Airport is Boeing 737-800, representing 23.20% of all bookings. The subsequent popular models are Boeing 737-700 Passenger/BBJ1 (winglets) at 10.77%, Embraer 175 (Enhanced Winglets) at 10.07%, and Boeing 737-800 Passenger/BBJ2 (winglets) at 9.98%.
What is the most popular airline from Hartford to Chicago Midway Airport?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Hartford to Chicago Midway Airport is Southwest (80% of total bookings). The next most popular airlines are Delta (8%), United Airlines (6%), and Frontier (6%).
Best airlines flying from Hartford to Chicago Midway Airport
Compare and see reviews for airlines that fly from Hartford to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $108 | Free Cancellation | Rating 5.9 3,290 reviews | |||
| PriceFrom $176 | Free Cancellation | Rating 8.0 7,973 reviews | |||
| PriceFrom $232 | Free Cancellation | Rating 8.0 4,278 reviews | |||
| PriceFrom $299 | Free Cancellation | Rating 7.4 8,852 reviews |
Southwest Flights From Hartford to Chicago Midway Airport
Southwest flies from Hartford to Chicago Midway Airport around 13 times per week, with 4,278 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Hartford to Chicago Midway Airport in the last 72 hours was $232 (round-trip), much lower than the average airfare cost of $372 for Southwest flights on this route.
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Why should I use momondo to find a flight deal from Hartford to Chicago?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Hartford to Chicago. momondo saves you time and could save you money on your trip.
Can I find flights from Hartford to Chicago with flexible booking policies on momondo?
All flight searches from Hartford to Chicago on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Hartford to Chicago?
momondo helps you find the best flight between Hartford and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.
I’m not ready to book a flight from Hartford to Chicago right now. Can momondo alert me if prices change?
Yes. momondo can track prices for Hartford to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.