Cheap flights from Chicago

We are watching 234 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 Charlotte €30 Quincy €38

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Where to fly from Chicago

Mon

4 Jan

Chicago → Fort Lauderdale

Frontier Airlines Based on 1716 observations ✈ Direct

United Airlines Based on 81 observations ✈ Direct

Contour Airlines Based on 62 observations ✈ Direct

Frontier Airlines Based on 573 observations ✈ Direct

Frontier Airlines Based on 300 observations ✈ Direct

American Airlines Based on 84 observations ✈ Direct

Southwest Airlines Based on 291 observations ✈ Direct

AA Based on 148 observations ✈ Direct

€65

Sun

15 Nov

Chicago → Indianapolis

American Airlines Based on 134 observations ✈ Direct

Frontier Airlines Based on 211 observations ✈ Direct

American Airlines Based on 114 observations ✈ Direct

American Airlines Based on 53 observations ✈ Direct

Frontier Airlines Based on 384 observations ✈ Direct

€72

Fri

13 Nov

Chicago → Knoxville/Maryville

Allegiant Air Based on 111 observations ✈ Direct

Frontier Airlines Based on 769 observations ✈ Direct

€73

Tue

1 Dec

Chicago → Dallas-Fort Worth

Frontier Airlines Based on 396 observations ✈ Direct

Frontier Airlines Based on 327 observations 1 stop

€75

Wed

9 Dec

Chicago → Cincinnati / Covington

Frontier Airlines Based on 98 observations 1 stop

Frontier Airlines Based on 741 observations 1 stop

Frontier Airlines Based on 227 observations 1 stop

American Airlines Based on 157 observations ✈ Direct

American Airlines Based on 201 observations ✈ Direct

€77

Thu

26 Nov

Chicago → Philadelphia

Frontier Airlines Based on 280 observations ✈ Direct

€79

Sun

22 Nov

Chicago → Minneapolis

Sun Country Airlines Based on 492 observations ✈ Direct

Frontier Airlines Based on 278 observations 1 stop

€82

Sat

14 Nov

Chicago → Cedar Rapids

American Airlines Based on 92 observations ✈ Direct

American Airlines Based on 47 observations ✈ Direct

American Airlines Based on 192 observations ✈ Direct

American Airlines Based on 68 observations ✈ Direct

American Airlines Based on 50 observations ✈ Direct

American Airlines Based on 36 observations ✈ Direct

American Airlines Based on 46 observations ✈ Direct

€86

Tue

19 Jan

Chicago → Los Angeles

Frontier Airlines Based on 639 observations 1 stop

Frontier Airlines Based on 492 observations 1 stop

Frontier Airlines Based on 1097 observations 1 stop

€91

Sun

15 Nov

Chicago → Raleigh/Durham

American Airlines Based on 96 observations ✈ Direct

American Airlines Based on 72 observations ✈ Direct

€91

Wed

11 Nov

Chicago → Bloomington/Normal

American Airlines Based on 17 observations ✈ Direct

€91

Sat

12 Dec

Chicago → New Orleans

Frontier Airlines Based on 296 observations 1 stop

Frontier Airlines Based on 267 observations 1 stop

jetBlue Based on 495 observations ✈ Direct

€94

Wed

2 Dec

Chicago → San Francisco

Frontier Airlines Based on 406 observations 1 stop

Frontier Airlines Based on 314 observations 1 stop

€97

Tue

1 Dec

Chicago → Jacksonville

Frontier Airlines Based on 194 observations 1 stop

€100

Sun

15 Nov

Chicago → Sioux Falls

American Airlines Based on 40 observations ✈ Direct

American Airlines Based on 28 observations ✈ Direct

€101

Sat

14 Nov

Chicago → Grand Rapids

American Airlines Based on 57 observations ✈ Direct

Frontier Airlines Based on 32 observations 1 stop

American Airlines Based on 55 observations ✈ Direct

€105

Thu

12 Nov

Chicago → Traverse City

American Airlines Based on 42 observations ✈ Direct

Alaska Airlines Based on 327 observations ✈ Direct

€108

Sat

30 Jan

Chicago → Guadalajara

Viva Aerobus Based on 200 observations ✈ Direct

€108

Tue

10 Nov

Chicago → Chattanooga

United Airlines Based on 16 observations ✈ Direct

Frontier Airlines Based on 71 observations 1 stop

Alaska Airlines Based on 173 observations 1 stop

American Airlines Based on 85 observations ✈ Direct

€115

Tue

10 Nov

Chicago → Springfield

American Airlines Based on 43 observations ✈ Direct

Denver Air Connection (DAC) Based on 35 observations ✈ Direct

American Airlines Based on 21 observations ✈ Direct

€116

Sun

15 Nov

Chicago → Salt Lake City

American Airlines Based on 132 observations ✈ Direct

€119

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 234 routes we track from Chicago. Next: Charlotte €30, Quincy €38, Atlanta €49.

What is the cheapest month to fly from Chicago?

November. On the 172 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 66 of the 182 routes from Chicago where we measured it.

Which airlines have the cheapest flights from Chicago?

American Airlines has the lowest fare on 61 of the 234 routes we track from Chicago, then Frontier Airlines (54), United Airlines (25), TAP Portugal (17), Icelandair (17).

How many routes from Chicago does Piratefly track?

234 routes, with 23,549 fares we have recorded over time.

Booking tips from our fare data

How far in advance should you book a flight?: Book 1.5–2 months before departure. Tracking the same flights at every lead time (103,225 flights on 20,679 routes, 2026-06-14 to 2026-11-07), that window had the smallest average premium over each flight's lowest fare: +16.4%, against +48.9% in the last 3 days.
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 -1.2% against the route's own median, while January 2027 was the dearest at +25.7%. Covers September 2026, October 2026, November 2026, December 2026, January 2027; fares observed 2026-06-14 to 2026-11-07.
Are flights getting more expensive?: Not right now. The Piratefly monthly Fare Index stands at 97.9 in 2026-11 (month in progress), against 100 in 2026-08: comparable flights are 2.1% cheaper than then, measured on the same routes month to month.