Earn point on your loyalty program!arrow arc left

Cheap flights from Tallahassee (TLH) to Chicago (CHI)

Know your dates, get live prices in seconds
airplane logo

pin logo

calendar
Departure
calendar backward
Return
airplane logo
1 Adults (11+)
0 Children (2~11)
0 Infants (0~2)
Save up to 31%
Book Flight + Hotel at the same time

How to find the cheapest flight from Tallahassee (TLH) to Chicago (CHI)

How to find the cheapest flight from Tallahassee (TLH) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Tallahassee (TLH) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Tallahassee (TLH) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.

Cheap flights from Tallahassee to Chicago in May , June 2026

30 May - 02 Jul $ 1,035.00
TLH
Tallahassee
BREEZE
3 STOPS
CHI
Chicago
CHI
Chicago
BREEZE
2 STOPS
TLH
Tallahassee
Pick dates
30 May - 02 Jul $ 1,129.00
TLH
Tallahassee
BREEZE
3 STOPS
CHI
Chicago
CHI
Chicago
BREEZE
3 STOPS
TLH
Tallahassee
Pick dates
28 May - 02 Jul $ 1,131.00
TLH
Tallahassee
BREEZE
3 STOPS
CHI
Chicago
CHI
Chicago
BREEZE
2 STOPS
TLH
Tallahassee
Pick dates

Last minute flights from Tallahassee to Chicago

27 May - 31 May $ 1,697.00
TLH
Tallahassee
AeroMéxico
3 STOPS
CHI
Chicago
CHI
Chicago
AeroMéxico
2 STOPS
TLH
Tallahassee
Pick dates
28 May - 31 May $ 1,722.00
TLH
Tallahassee
AeroMéxico
3 STOPS
CHI
Chicago
CHI
Chicago
AeroMéxico
2 STOPS
TLH
Tallahassee
Pick dates
26 May - 31 May $ 1,832.00
TLH
Tallahassee
AeroMéxico
3 STOPS
CHI
Chicago
CHI
Chicago
AeroMéxico
2 STOPS
TLH
Tallahassee
Pick dates

One-way flights to Chicago from Tallahassee

2:43 PM - 1:45 PM
Porter Airlines
3 Stops
24h 52m
TLH - CHI
$ 803
Kiwi
Pick dates
7:07 PM - 8:58 PM
Frontier Airlines
3 Stops
29h 6m
TLH - CHI
$ 869
Kiwi
Pick dates
7:07 PM - 8:55 AM
Porter Airlines
3 Stops
15h 38m
TLH - CHI
$ 894
Kiwi
Pick dates

How to find the cheapest flight from Tallahassee (TLH) to Chicago (CHI)

Related info for your journey
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Tallahassee (TLH) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Tallahassee (TLH) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.