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Cheap Flights from Hartford Bradley International to Chicago Midway

Compare Hartford Bradley International to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from Hartford Bradley International to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Hartford Bradley International to Chicago Midway? Find the lowest prices on one-way and return tickets right here.
Chicago.118 € per passenger.Departing Thu, 2 Oct, returning Sun, 5 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Hartford Bradley International on Thu, 2 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 5 Oct, arriving in Hartford Bradley International.Price includes taxes and charges.From 118 €, select.
Chicago.148 € per passenger.Departing Thu, 11 Sep, returning Sun, 14 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Hartford Bradley International on Thu, 11 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 14 Sep, arriving in Hartford Bradley International.Price includes taxes and charges.From 148 €, select.
Chicago.169 € per passenger.Departing Sun, 20 Jul, returning Tue, 22 Jul.Return flight with Delta.Outbound indirect flight with Delta, departs from Hartford Bradley International on Sun, 20 Jul, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Tue, 22 Jul, arriving in Hartford Bradley International.Price includes taxes and charges.From 169 €, select.
Chicago.178 € per passenger.Departing Sat, 30 Aug, returning Tue, 2 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Hartford Bradley International on Sat, 30 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 2 Sep, arriving in Hartford Bradley International.Price includes taxes and charges.From 178 €, select.
Chicago.179 € per passenger.Departing Thu, 7 Aug, returning Tue, 12 Aug.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Hartford Bradley International on Thu, 7 Aug, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 12 Aug, arriving in Hartford Bradley International.Price includes taxes and charges.From 179 €, select.
Chicago.188 € per passenger.Departing Sat, 19 Jul, returning Tue, 22 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Hartford Bradley International on Sat, 19 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 22 Jul, arriving in Hartford Bradley International.Price includes taxes and charges.From 188 €, select.
Chicago.212 € per passenger.Departing Tue, 29 Jul, returning Sat, 2 Aug.Return flight with Delta.Outbound indirect flight with Delta, departs from Hartford Bradley International on Tue, 29 Jul, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sat, 2 Aug, arriving in Hartford Bradley International.Price includes taxes and charges.From 212 €, select.
Chicago.217 € per passenger.Departing Tue, 29 Jul, returning Sat, 2 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Hartford Bradley International on Tue, 29 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 2 Aug, arriving in Hartford Bradley International.Price includes taxes and charges.From 217 €, select.

Find the cheapest month to fly from Hartford Bradley International to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Hartford Bradley International to Chicago Midway flights are currently cheapest in October.
Jun
from 235 €
Jul
from 169 €
Aug
from 179 €
Sep
from 148 €
Oct
from 118 €
Nov
Find prices
Dec
from 305 €
Jan
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Feb
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Mar
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Apr
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May
from 358 €

Direct flights from Hartford Bradley International to Chicago Midway

Hartford Bradley International to Chicago Midway: Alternative routes

Compare routes from Hartford Bradley International to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Hartford to Chicago: Flight information

The things to know before you go.
Cheapest flight found118 €
Cheapest month to flyOctober
Average flight time2 hrs, 26 mins
Most popular airlineSouthwest Airlines
Average flights per week17

Finding cheap flights from Hartford Bradley International to Chicago Midway: Frequently asked questions

The best price we found for a return flight from Hartford Bradley International to Chicago Midway is 118 €. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 26 minutes is the average flight time from Hartford Bradley International to Chicago Midway.
Southwest Airlines flies direct from Hartford Bradley International to Chicago Midway.
As of June 2025, there are 17 flights per week flying from Hartford Bradley International to Chicago Midway.
The cheapest month to fly from Hartford Bradley International to Chicago Midway is usually June 2025.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Hartford Bradley International Airport to Chicago Midway Airport on Thursday, 2 October 2025.
Yes – the average flight time is 2 hours and 26 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Southwest Airlines offers the cheapest flight tickets to Chicago Midway.

Travelling from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW): what you need to know

  • The average length of a direct flight from Bradley International Airport to Chicago Midway International Airport is 2 hours 25 minutes.

  • Chicago is one hour behind Hartford and follows the UTC-5 timezone.

  • Take your pick of 12 weekly Bradley International Airport to Chicago Midway International Airport flights. The 05:05 departure with Southwest Airlines is the earliest available. Southwest Airlines operates the last service of the day at 20:25.

  • Your BDL to MDW flight won't wait if you're running late, so don't forget to check in on time. Arrive up to one hour in advance for domestic flights and two hours ahead for international travel.

  • Be prepared for longer lines during popular months like August. Arriving up to four hours ahead of an international flight and two hours for domestic departures will help ensure a smooth travel experience.

  • Southwest Airlines offers direct flights from Bradley International Airport to Chicago Midway International Airport. Book with this popular airline, then get ready to tick off the sights in Chicago — and maybe even more of United States if your schedule allows.

  • The airline that tops the list for bookings on this route is Southwest Airlines.

  • Southwest Airlines tops the rankings as the most punctual carrier for BDL to MDW flights, with 87.16% of services landing as scheduled.

  • If you'd like to include a stop along the way, simply deselect 'Direct flights only' when searching for your ticket from Bradley International Airport to Chicago Midway International Airport. Here are the top stopovers between BDL and MDW:

    • John Glenn Columbus International Airport

    • Baltimore/Wash International Thurgood Marshall Airport

    • Detroit Metropolitan Wayne County Airport

How to find the cheapest flights from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)

  • The lowest price we've found for a one-way Bradley International Airport to Chicago Midway International Airport flight is 59 €. A return plane ticket right now is 118 €. Depending on the availability when you book, these fares can change.

  • Book six months before flying. After looking at the numbers on our calendar, this is how far you should book ahead to secure cheap tickets from BDL to MDW.

  • The cheapest month for flights from Bradley International Airport to Chicago Midway International Airport is May. Use the 'Whole month' tool to see the lowest prices if you have a flexible travel schedule.

  • Getting your hands on cheap flights from BDL to MDW is a breeze with Price Alerts. Simply create one of these automatic alerts and we'll get in touch as soon as a new discounted fare appears.

  • Tailor your flights with filters. Pick your ideal arrival and departure times, total journey duration and airlines. You can also sort your results by 'Best,' 'Cheapest' or 'Fastest' flights from Bradley International Airport to Chicago Midway International Airport.

Handy information about Bradley International Airport (BDL)

  • BDL is located at Schoephoester Road.

  • Bradley International Airport maintains a solid on-time performance, so flight disruptions are less likely. Departures from BDL land at their destination as scheduled 80.22% of the time.

  • Bradley International Airport is around 24 kilometres from central Hartford. If you're driving, catching a cab or ride-sharing from the centre, it'll take 15 minutes or so to get there, depending on the traffic.

  • You can expect a journey time of around 30 minutes on public transport.

  • Get your travels off to a stress-free start by staying near BDL. Whether you're boarding an early flight from Bradley International Airport to Chicago Midway International Airport or just don't want to be rushed, these stays are perfect:

Arriving at Chicago Midway International Airport (MDW)

  • The last thing you need is a lengthy journey to your hotel if you're arriving on a late Bradley International Airport to Chicago Midway International Airport flight. Reserve one of these accommodation options near MDW instead:

  • Pick up a Chicago Midway International Airport rental car and discover Chicago and beyond with your own set of wheels. Dollar, Hertz and Budget are popular providers you can book with here.

  • Lock in the lowest price by reserving your vehicle from Chicago Midway International Airport around four weeks before your travel date.

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • MDW is located at 5700 South Cicero.

  • Chicago Midway International Airport to the centre of Chicago has a drive time of about 20 minutes. It's approximately 19 kilometres away.

  • Getting there on public transport typically takes 45 minutes.

When to fly to Chicago Midway International Airport (MDW)

  • It's time to choose your travel dates for your flight from Bradley International Airport to Chicago Midway International Airport. July is the busiest month to visit Chicago. If you want a more low-key vibe, go in May.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC (59ºF) and 29ºC (84ºF). Lock in your flights from Bradley International Airport to Chicago Midway International Airport in this month if this is the type of weather you like.

  • If you want to travel in cooler conditions, look for a cheap ticket from BDL to MDW in January. Temperatures average between -12ºC (10ºF) and 3ºC (37ºF) then.

Explore more of United States

  • Columbus is just one of the many places in United States waiting to be discovered once you've taken in the sights of Chicago. Around 451 kilometres away to the south-east, its top attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • If you're ready to explore another great destination in United States, consider Indianapolis, roughly 257 kilometres south-east of Chicago. The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo are key reasons to visit.

Plan the rest of your trip from Hartford to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.