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243 € 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 Airport to Chicago Midway Airport? If you want to travel next month, return fares start from 243 €. Find the lowest prices on one-way and return tickets right here.
Chicago.243 € per passenger.Departing Tue, 1 Dec, returning Tue, 8 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Hartford Bradley International on Tue, 1 Dec, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 8 Dec, arriving in Hartford Bradley International.Price includes taxes and charges.From 243 €, select.
Chicago.243 € per passenger.Departing Mon, 16 Nov, returning Mon, 23 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Hartford Bradley International on Mon, 16 Nov, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 23 Nov, arriving in Hartford Bradley International.Price includes taxes and charges.From 243 €, select.
Chicago.243 € per passenger.Departing Tue, 15 Sep, returning Mon, 21 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Hartford Bradley International on Tue, 15 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 21 Sep, arriving in Hartford Bradley International.Price includes taxes and charges.From 243 €, select.
Chicago.243 € per passenger.Departing Tue, 20 Oct, returning Sat, 24 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Hartford Bradley International on Tue, 20 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 24 Oct, arriving in Hartford Bradley International.Price includes taxes and charges.From 243 €, select.
Chicago.243 € per passenger.Departing Wed, 20 Jan, returning Tue, 26 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Hartford Bradley International on Wed, 20 Jan, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 26 Jan, arriving in Hartford Bradley International.Price includes taxes and charges.From 243 €, select.
Chicago.243 € per passenger.Departing Sat, 29 Aug, returning Tue, 1 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Hartford Bradley International on Sat, 29 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 1 Sep, arriving in Hartford Bradley International.Price includes taxes and charges.From 243 €, select.
Chicago.243 € per passenger.Departing Mon, 17 Aug, returning Thu, 20 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Hartford Bradley International on Mon, 17 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 20 Aug, arriving in Hartford Bradley International.Price includes taxes and charges.From 243 €, select.
Chicago.243 € per passenger.Departing Thu, 26 Nov, returning Thu, 3 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Hartford Bradley International on Thu, 26 Nov, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 3 Dec, arriving in Hartford Bradley International.Price includes taxes and charges.From 243 €, select.
Chicago.266 € per passenger.Departing Tue, 29 Sep, returning Wed, 7 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Hartford Bradley International on Tue, 29 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 7 Oct, arriving in Hartford Bradley International.Price includes taxes and charges.From 266 €, select.
Chicago.299 € per passenger.Departing Tue, 2 Feb, returning Fri, 5 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Hartford Bradley International on Tue, 2 Feb, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 5 Feb, arriving in Hartford Bradley International.Price includes taxes and charges.From 299 €, select.
Chicago.363 € per passenger.Departing Thu, 6 May, returning Tue, 11 May.Return flight with Delta.Outbound indirect flight with Delta, departs from Hartford Bradley International on Thu, 6 May, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Tue, 11 May, arriving in Hartford Bradley International.Price includes taxes and charges.From 363 €, select.
Chicago.378 € per passenger.Departing Fri, 12 Mar, returning Sun, 14 Mar.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Hartford Bradley International on Fri, 12 Mar, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 14 Mar, arriving in Hartford Bradley International.Price includes taxes and charges.From 378 €, select.
Chicago.450 € per passenger.Departing Thu, 30 Jul, returning Tue, 4 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Hartford Bradley International on Thu, 30 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 4 Aug, arriving in Hartford Bradley International.Price includes taxes and charges.From 450 €, select.
Chicago.510 € per passenger.Departing Sun, 11 Apr, returning Fri, 16 Apr.Return flight with Delta.Outbound indirect flight with Delta, departs from Hartford Bradley International on Sun, 11 Apr, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Fri, 16 Apr, arriving in Hartford Bradley International.Price includes taxes and charges.From 510 €, 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 August.
Jul
Find prices
Aug
from 243 €
Sep
from 243 €
Oct
from 243 €
Nov
from 243 €
Dec
from 243 €
Jan
from 243 €
Feb
from 299 €
Mar
from 378 €
Apr
from 510 €
May
from 363 €
Jun
Find prices

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.

Chicago Midway

14km from central Chicago
Closest
from 243 €
Search flights

Chicago O'Hare International

25km from central Chicago
Cheapest
from 180 €
Search flights

Chicago Rockford

127km from central Chicago
from 295 €
Search flights

Hartford to Chicago: Flight information

The things to know before you go.
Cheapest flight found243 €
Cheapest month to flyNovember
Average flight time2 hrs, 27 mins
Most popular airlineSouthwest Airlines
Average flights per week24

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 243 €. 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 27 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 July 2026, there are 24 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 November.
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, 26 November 2026.
Yes – the average flight time is 2 hours and 27 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.

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

  • Around 2 hours 25 minutes is how long you can expect to be in the air on a direct flight from Hartford Bradley International Airport to Chicago Midway Airport.

  • Chicago is one hour behind Hartford and is in the UTC-6 timezone.

  • You can choose from 11 weekly Hartford Bradley International Airport to Chicago Midway Airport flights. The 05:05 departure with Southwest Airlines is the earliest flight available. Southwest Airlines operates the last service of the day at 20:20.

  • Arriving two hours before an international flight and one hour ahead of a domestic departure are golden rules for stress-free travel. Be at the airport on time to catch your BDL to MDW flight.

  • You can expect longer queues during popular months such as August. Arriving up to four hours ahead of an international flight and two hours for domestic departures is a smart move.

  • Jetting into Chicago (and then discovering more of the United States!) is a breeze with Southwest Airlines. This popular carrier has direct flights from Hartford Bradley International Airport to Chicago Midway Airport.

  • The majority of travellers choose to fly with Southwest Airlines on this route.

  • Southwest Airlines is the most punctual carrier that offers BDL to MDW flights. An impressive 84.91% of its services on this route arrive as scheduled.

  • If you'd like to break up your flight, simply uncheck 'Direct flights only' when searching for your ticket from Hartford Bradley International Airport to Chicago Midway Airport. Here are the most popular stopovers between BDL and MDW:

    • Detroit Wayne County Airport

    • Baltimore Washington International Airport

    • Port Columbus Airport

Handy information about Hartford Bradley International Airport (BDL)

Arriving at Chicago Midway Airport (MDW)

  • If you're coming in on a late Hartford Bradley International Airport to Chicago Midway Airport flight, nothing tops the convenience of being close to the terminal. Collect your bags from the carousel and then be showered and snoozing not long after at one of these accommodation options near MDW:

  • Travel at your own speed with a Chicago Midway Airport rental car. Book your wheels from Dollar, Hertz or Budget and discover more of Chicago and beyond.

  • Reserving your vehicle from Chicago Midway Airport around four weeks ahead gives you the best shot at securing a great deal.

Getting from Chicago Midway Airport (MDW) to central Chicago

  • You'll find MDW at 5700 South Cicero.

  • From Chicago Midway Airport, Chicago is approximately 16 kilometres away. It takes around 25 minutes to reach the centre driving.

  • Getting there on public transport will take you roughly 30 minutes.

When to fly to Chicago Midway Airport (MDW)

  • The quietest month for a flight from Hartford Bradley International Airport to Chicago Midway Airport is December, while July is the busiest. Pick the ideal time to visit Chicago based on whether you prefer a bustling atmosphere or a more laid-back vibe.

  • The warmest month in Chicago is July, with temperatures ranging between 16ºC (61ºF) and 28ºC (82ºF). Book your flights from Hartford Bradley International Airport to Chicago Midway Airport in this month if this is the type of weather you enjoy.

  • Look for cheap tickets from BDL to MDW in January if you like cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

Explore more of the United States

  • Chicago has plenty to offer, but there are so many other parts of the United States just waiting to be explored. Around 451 kilometres south-east of Chicago, a visit to Columbus will keep you on the go. Start with attractions like Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

  • Indianapolis is another must-experience destination in the United States and is around 257 kilometres south-east of Chicago. No trip is complete without visiting Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

Plan the rest of your trip from Hartford to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.