Cheap flights from Chicago

We are watching 231 routes out of Chicago. The cheapest fare we can vouch for today is €22, and for each one we say whether today is a good moment or you should wait.

See this fare · Fort Lauderdale €22 Baltimore €30 Charlotte €30

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Where to fly from Chicago

Mon

4 Jan

Chicago → Fort Lauderdale

Frontier Airlines Based on 1666 observations ✈ Direct

Frontier Airlines Based on 371 observations ✈ Direct

United Airlines Based on 74 observations ✈ Direct

Contour Airlines Based on 58 observations ✈ Direct

Frontier Airlines Based on 559 observations ✈ Direct

Frontier Airlines Based on 292 observations ✈ Direct

Southwest Airlines Based on 283 observations ✈ Direct

American Airlines Based on 80 observations ✈ Direct

Frontier Airlines Based on 304 observations 1 stop

Frontier Airlines Based on 719 observations 1 stop

€62

Sun

15 Nov

Chicago → Indianapolis

American Airlines Based on 126 observations ✈ Direct

Frontier Airlines Based on 199 observations ✈ Direct

Frontier Airlines Based on 260 observations ✈ Direct

American Airlines Based on 106 observations ✈ Direct

American Airlines Based on 49 observations ✈ Direct

€71

Fri

13 Nov

Chicago → Knoxville/Maryville

Allegiant Air Based on 105 observations ✈ Direct

Frontier Airlines Based on 754 observations ✈ Direct

Frontier Airlines Based on 274 observations ✈ Direct

€74

Tue

1 Dec

Chicago → Dallas-Fort Worth

Frontier Airlines Based on 388 observations ✈ Direct

Frontier Airlines Based on 314 observations 1 stop

€75

Wed

9 Dec

Chicago → Cincinnati / Covington

Frontier Airlines Based on 91 observations 1 stop

Frontier Airlines Based on 210 observations 1 stop

American Airlines Based on 153 observations ✈ Direct

American Airlines Based on 195 observations ✈ Direct

€77

Thu

26 Nov

Chicago → Philadelphia

Frontier Airlines Based on 276 observations ✈ Direct

American Airlines Based on 140 observations ✈ Direct

€79

Sun

22 Nov

Chicago → Minneapolis

Sun Country Airlines Based on 474 observations ✈ Direct

Frontier Airlines Based on 468 observations 1 stop

€80

Thu

3 Dec

Chicago → San Francisco

Frontier Airlines Based on 399 observations 1 stop

€81

Sat

14 Nov

Chicago → Cedar Rapids

American Airlines Based on 86 observations ✈ Direct

American Airlines Based on 188 observations ✈ Direct

American Airlines Based on 62 observations ✈ Direct

American Airlines Based on 46 observations ✈ Direct

American Airlines Based on 32 observations ✈ Direct

€84

Tue

24 Nov

Chicago → Raleigh/Durham

Frontier Airlines Based on 92 observations 1 stop

American Airlines Based on 43 observations ✈ Direct

€86

Tue

19 Jan

Chicago → Los Angeles

Frontier Airlines Based on 609 observations 1 stop

American Airlines Based on 43 observations ✈ Direct

American Airlines Based on 68 observations ✈ Direct

€91

Wed

11 Nov

Chicago → Bloomington/Normal

American Airlines Based on 14 observations ✈ Direct

American Airlines Based on 1077 observations ✈ Direct

€92

Sat

12 Dec

Chicago → New Orleans

Frontier Airlines Based on 286 observations 1 stop

jetBlue Based on 489 observations ✈ Direct

€94

Sun

15 Nov

Chicago → Sioux Falls

American Airlines Based on 36 observations ✈ Direct

Frontier Airlines Based on 258 observations 1 stop

€102

Sat

14 Nov

Chicago → Grand Rapids

American Airlines Based on 53 observations ✈ Direct

Frontier Airlines Based on 28 observations 1 stop

American Airlines Based on 51 observations ✈ Direct

€105

Thu

12 Nov

Chicago → Traverse City

American Airlines Based on 38 observations ✈ Direct

Frontier Airlines Based on 324 observations 1 stop

€108

Sat

30 Jan

Chicago → Guadalajara

Viva Aerobus Based on 190 observations ✈ Direct

American Airlines Based on 24 observations ✈ Direct

€108

Tue

10 Nov

Chicago → Chattanooga

United Airlines Based on 14 observations ✈ Direct

Denver Air Connection (DAC) Based on 33 observations ✈ Direct

Alaska Airlines Based on 163 observations 1 stop

Frontier Airlines Based on 68 observations 1 stop

€111

Wed

2 Dec

Chicago → Sarasota/Bradenton

Frontier Airlines Based on 40 observations 2 stops

€114

Mon

30 Nov

Chicago → Jacksonville

Frontier Airlines Based on 187 observations 1 stop

American Airlines Based on 81 observations ✈ Direct

€115

Tue

10 Nov

Chicago → Springfield

American Airlines Based on 37 observations ✈ Direct

€115

Flights from Chicago: quick answers

What is the cheapest flight from Chicago right now?

Fort Lauderdale at €22 one-way, the lowest fare today across the 231 routes we track from Chicago. Next: Baltimore €30, Charlotte €30, Quincy €38.

What is the cheapest month to fly from Chicago?

November. On the 173 routes from Chicago where we measured it, November fares were typically 5% below the route's median month.

How far in advance should I book flights from Chicago?

0–13 days before departure: that has been the cheapest booking window on 64 of the 183 routes from Chicago where we measured it.

Which airlines have the cheapest flights from Chicago?

American Airlines has the lowest fare on 57 of the 231 routes we track from Chicago, then Frontier Airlines (55), United Airlines (26), TAP Portugal (21), Icelandair (17).

How many routes from Chicago does Piratefly track?

231 routes, with 22,653 fares we have recorded over time.

Booking tips from our fare data

How far in advance should you book a flight?: Book 1–1.5 months before departure. Tracking the same flights at every lead time (97,668 flights on 19,841 routes, 2026-06-14 to 2026-11-05), that window had the smallest average premium over each flight's lowest fare: +16.7%, against +49.3% in the last 3 days.
What is the cheapest day of the week to fly?: Wednesday. Comparing each fare with the median of its own route, Wednesday departures were +3.5% and Tuesday +4.3%, while Friday was the dearest at +10.5%. Weekend departures cost more than midweek ones.
What is the cheapest month to fly?: November 2026. Comparing each route's fares month by month (booked 8–60 days ahead), November 2026 departures were -1.1% against the route's own median, while January 2027 was the dearest at +22.7%. Covers September 2026, October 2026, November 2026, December 2026, January 2027; fares observed 2026-06-14 to 2026-11-05.