Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline Frontier Airlines
Cheapest Month May
Cheapest Day of the Week Sunday
Cheapest Airline Frontier Airlines

The cheapest airline(s) flying from Hartford to Chicago is Frontier Airlines.

  • Frontier Airlines Frontier Airlines
  • Spirit Airlines Spirit Airlines
  • American Airlines American Airlines
  • Southwest Airlines Southwest Airlines
  • United Airlines United Airlines
  • JetBlue Airways JetBlue Airways
Cheapest Month May

Travel Period: April 2025 - March 2026

The cheapest month(s) to fly from Hartford to Chicago is May.

  • Apr 2025
  • May 2025
  • Jun 2025
  • Jul 2025
  • Aug 2025
  • Sep 2025
  • Oct 2025
  • Nov 2025
  • Dec 2025
  • Jan 2026
  • Feb 2026
  • Mar 2026
Cheapest Day of the Week Sunday

The cheapest day(s) of the week to fly from Hartford to Chicago is Sunday.

  • Sun Sunday
  • Mon Monday
  • Tue Tuesday
  • Wed Wednesday
  • Thu Thursday
  • Fri Friday
  • Sat Saturday

Flight Schedules

Last Updated: Sun, 2 Mar, 2025

  • Time Earliest
    • Earliest
    • Latest
  • Depart Earliest
    • Earliest
    • Latest
  • Arrive
    • Earliest
    • Latest
  • Duration
    • Shortest
    • Longest
  • Stopover
    All
    • Airline Filter by Airline
      View All Airline
      • Availability
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 20:20 BDL
        21:50 MDW
        2Hrs, 30m Direct
      • BDLHartford Bradley International Airport 20:20 - MDW 21:50 2h 30m Direct
      • BDLHartford Bradley International Airport 20:20
      • MDWChicago Midway Airport 21:50
      • 2h 30m
      • Direct
      • Southwest Airlines (WN 3723)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3723)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 05:05 BDL
        06:35 MDW
        2Hrs, 30m Direct
      • BDLHartford Bradley International Airport 05:05 - MDW 06:35 2h 30m Direct
      • BDLHartford Bradley International Airport 05:05
      • MDWChicago Midway Airport 06:35
      • 2h 30m
      • Direct
      • Southwest Airlines (WN 1435)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1435)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 06:00 BDL
        07:55 ORD
        2Hrs, 55m Direct
      • BDLHartford Bradley International Airport 06:00 - ORD 07:55 2h 55m Direct
      • BDLHartford Bradley International Airport 06:00
      • ORDChicago O'Hare International Airport 07:55
      • 2h 55m
      • Direct
      • United Airlines (UA 1304)Airbus
      • United Airlines (UA 1304)
        • -
        • T
        • -
        • -
        • -
        • -
        • S
      • Airbus
      • 06:00 BDL
        07:55 ORD
        2Hrs, 55m Direct
      • BDLHartford Bradley International Airport 06:00 - ORD 07:55 2h 55m Direct
      • BDLHartford Bradley International Airport 06:00
      • ORDChicago O'Hare International Airport 07:55
      • 2h 55m
      • Direct
      • United Airlines (UA 1304)Boeing 737 900
      • United Airlines (UA 1304)
        • M
        • -
        • W
        • T
        • F
        • S
        • -
      • Boeing 737 900
      • 06:00 BDL
        07:30 MDW
        2Hrs, 30m Direct
      • BDLHartford Bradley International Airport 06:00 - MDW 07:30 2h 30m Direct
      • BDLHartford Bradley International Airport 06:00
      • MDWChicago Midway Airport 07:30
      • 2h 30m
      • Direct
      • Southwest Airlines (WN 1435)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1435)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 06:32 BDL
        08:15 ORD
        2Hrs, 43m Direct
      • BDLHartford Bradley International Airport 06:32 - ORD 08:15 2h 43m Direct
      • BDLHartford Bradley International Airport 06:32
      • ORDChicago O'Hare International Airport 08:15
      • 2h 43m
      • Direct
      • American Airlines (AA 1021)Boeing 737 800
      • American Airlines (AA 1021)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • Boeing 737 800
      • 06:45 BDL
        08:15 MDW
        2Hrs, 30m Direct
      • BDLHartford Bradley International Airport 06:45 - MDW 08:15 2h 30m Direct
      • BDLHartford Bradley International Airport 06:45
      • MDWChicago Midway Airport 08:15
      • 2h 30m
      • Direct
      • Southwest Airlines (WN 1435)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1435)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 07:05 BDL
        08:35 MDW
        2Hrs, 30m Direct
      • BDLHartford Bradley International Airport 07:05 - MDW 08:35 2h 30m Direct
      • BDLHartford Bradley International Airport 07:05
      • MDWChicago Midway Airport 08:35
      • 2h 30m
      • Direct
      • Southwest Airlines (WN 1435)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1435)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 Max 8 Passenger
      • 07:10 BDL
        08:53 ORD
        2Hrs, 43m Direct
      • BDLHartford Bradley International Airport 07:10 - ORD 08:53 2h 43m Direct
      • BDLHartford Bradley International Airport 07:10
      • ORDChicago O'Hare International Airport 08:53
      • 2h 43m
      • Direct
      • American Airlines (AA 1021)Boeing 737 800
      • American Airlines (AA 1021)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 11:45 BDL
        13:46 ORD
        3Hrs, 01m Direct
      • BDLHartford Bradley International Airport 11:45 - ORD 13:46 3h 01m Direct
      • BDLHartford Bradley International Airport 11:45
      • ORDChicago O'Hare International Airport 13:46
      • 3h 01m
      • Direct
      • United Airlines (UA 4657)Embraer 175
      • United Airlines (UA 4657)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • Embraer 175
      • 12:21 BDL
        14:10 ORD
        2Hrs, 49m Direct
      • BDLHartford Bradley International Airport 12:21 - ORD 14:10 2h 49m Direct
      • BDLHartford Bradley International Airport 12:21
      • ORDChicago O'Hare International Airport 14:10
      • 2h 49m
      • Direct
      • American Airlines (AA 4524)Embraer Emb 175
      • American Airlines (AA 4524)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Embraer Emb 175
      • 16:55 BDL
        18:48 ORD
        2Hrs, 53m Direct
      • BDLHartford Bradley International Airport 16:55 - ORD 18:48 2h 53m Direct
      • BDLHartford Bradley International Airport 16:55
      • ORDChicago O'Hare International Airport 18:48
      • 2h 53m
      • Direct
      • United Airlines (UA 1846)Boeing 737 800
      • United Airlines (UA 1846)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 800
      • 18:01 BDL
        19:44 ORD
        2Hrs, 43m Direct
      • BDLHartford Bradley International Airport 18:01 - ORD 19:44 2h 43m Direct
      • BDLHartford Bradley International Airport 18:01
      • ORDChicago O'Hare International Airport 19:44
      • 2h 43m
      • Direct
      • American Airlines (AA 3370)Embraer 170
      • American Airlines (AA 3370)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • Embraer 170
      • 18:01 BDL
        19:50 ORD
        2Hrs, 49m Direct
      • BDLHartford Bradley International Airport 18:01 - ORD 19:50 2h 49m Direct
      • BDLHartford Bradley International Airport 18:01
      • ORDChicago O'Hare International Airport 19:50
      • 2h 49m
      • Direct
      • American Airlines (AA 4521)Embraer Emb 175
      • American Airlines (AA 4521)
        • -
        • T
        • W
        • -
        • -
        • S
        • -
      • Embraer Emb 175
      No Schedules Sorry, there are no schedules matching your filters. Try removing one. reset
      What’s the fastest flight time from Hartford to Chicago?

      The fastest flight time for direct flights from Hartford to Chicago is 2 hours 30 minutes. Check latest flight schedules & prices on Wego.

      What’s the most popular airline flying from Hartford to Chicago?

      The most popular airline flying from Hartford to Chicago is American Airlines. Find the latest flight deals on Wego.

      How far is Chicago from Hartford?

      The flight distance between Hartford and Chicago is 1237km. Check all available flights on Wego.

      When is the earliest and latest flight of the day?

      The earliest flight of the day departs at 05:05. The last flight of the day departs at 20:20. See the full list of flight times on Wego.

      How many airlines offer direct flights from Hartford to Chicago?

      There are 3 airlines that offer direct flights from Hartford to Chicago. Find out the list of airlines on Wego.

      All Airports in Hartford

      Hartford Bradley International Airport BDL

      Brainard Airport HFD

      Popular Airlines Flying From Hartford to Chicago

      American Airlines ‏()
      Frontier Airlines ‏()
      Spirit Airlines ‏()
      United Airlines ‏()

      Popular Destinations From Chicago

      Popular Destinations From Hartford

      Popular Hotels in Chicago

      Hotels In Popular Destinations