$79+ Cheap flights from Connecticut to Midway (MDW)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Connecticut to Midway with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Connecticut to Midway
Keep the following information in mind while searching for Connecticut to Midway flight deals. Data was last updated June 12, 2025.
Round-trip from | $137 (Southwest) |
|---|---|
One-way from | $79 (Delta) |
Good round-trip deal | $355 or less |
Good one-way deal | $195 or less |
Find flight deals from Connecticut to Midway
Cheapest flights from Connecticut to MidwayExplore the most affordable flight options available from Connecticut to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.
Explore the most affordable flight options available from Connecticut to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Frontier deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Booking.com deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Frontier deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Cheapflights Fare Finder
Customize your flight search to find flights from Connecticut to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
Use the filters below to find and compare flights from Connecticut to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Thu 7/10
9:05 am-10:30 am
Nonstop2h 25m
Chicago Midway
Sat 7/12
7:00 pm-10:10 pm
Nonstop2h 10m
NewarkChicago
EWR - MDW
EWRMDW
Newark
Wed 7/9
6:00 am-8:44 am
1 stop3h 44m
Chicago Midway
Wed 7/9
5:05 pm-12:59 am
1 stop6h 54m
NewarkChicago
EWR - MDW
EWRMDW
Newark
Tue 6/17
5:59 am-10:41 am
1 stop5h 42m
Chicago Midway
Wed 6/18
11:39 am-12:44 am
1 stop12h 05m
New YorkChicago
JFK - MDW
JFKMDW
New York John F Kennedy Intl
Tue 9/9
1:01 pm-10:58 pm
1 stop10h 57m
Chicago Midway
Tue 9/16
8:00 am-12:40 am
1 stop15h 40m
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Wed 9/10
6:30 am-10:58 pm
1 stop17h 28m
Chicago Midway
Wed 9/24
8:00 am-11:32 pm
1 stop14h 32m
ProvidenceChicago
PVD - MDW
PVDMDW
Providence-TFGreen
Fri 9/12
5:55 pm-7:20 pm
Nonstop2h 25m
Chicago Midway
Mon 9/15
9:55 am-1:15 pm
Nonstop2h 20m
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Sat 11/8
9:45 am-6:45 pm
2 stops10h 00m
Chicago Midway
Mon 11/10
11:55 am-2:55 pm
Nonstop2h 00m
NewarkChicago
EWR - MDW
EWRMDW
Newark
Fri 8/1
9:55 am-1:56 pm
1 stop5h 01m
Chicago Midway
Mon 8/4
1:11 pm-9:05 am
1 stop18h 54m
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Sun 8/31
1:00 pm-6:37 pm
1 stop6h 37m
Chicago Midway
Wed 9/3
10:11 am-5:59 pm
1 stop6h 48m
ProvidenceChicago
PVD - MDW
PVDMDW
Providence-TFGreen
Thu 8/21
5:54 am-8:35 am
1 stop3h 41m
Chicago Midway
Mon 8/25
6:17 pm-11:09 pm
1 stop3h 52m
Best time to book a flight from Connecticut to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Connecticut with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Connecticut to Chicago Midway Airport
What is the cheapest month to book a flight from Connecticut to Chicago Midway Airport?
Currently, April is the cheapest month in which you can book a flight from Connecticut to Chicago Midway Airport (average of $160). Flying from Connecticut to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CT to MDW?
Find hourly flight availability from Connecticut to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 12, 2025.
When flying from Connecticut to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Rainfall in Midway by month
Plan your trip to Midway by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.
Temperature in Midway by month
Plan your trip to Midway by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated June 12, 2025.
To help decide which airline to fly from Connecticut to Chicago, see what other customers have to say about Southwest, Delta and Allegiant Air. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
Boarding
Crew
Entertainment
Comfort
Overall
Reviews
John,May 2025
PVD - BNA
Food
Boarding
Crew
Entertainment
Comfort
Overall
Reviews
John,May 2025
PVD - BNA
Food
Boarding
Crew
Entertainment
Comfort
Overall
Reviews
John,May 2025
PVD - BNA
Food
Boarding
Crew
Entertainment
Comfort
Overall
Reviews
John,May 2025
PVD - BNA
Food
Boarding
Crew
Entertainment
Comfort
Overall
Reviews
John,May 2025
PVD - BNA
Related info for your journey
Find useful and relevant information for your journey from Connecticut to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Connecticut to Midway
See prices for flight routes from nearby airports that may be better suited for you.
Top 5 airlines flying from Connecticut to Midway
Discover the top 5 airlines that operate flights from Connecticut to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$77 | Average$176 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$108 | Average$257 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$125 | Average$471 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$176 | Average$346 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$232 | Average$379 | FlexibilityNo cancel fee | On-time63% |