Cheap flights from Chicago from $30

Compare flights from Chicago and book wherever you prefer

We compare all the airline and agency websites to find the cheapest flight with origin in Chicago. Find your flight from Chicago using Trabber and book it directly on the website with the best price, saving time and money.

Information about flights from Chicago

Minimum price $30
Average price $571
Popular airline Volaris
Cheap month November
High season June
Best getaway departing: Wednesday, returning: Thursday
Best time to buy 80 days in advance

Cheapest flights to popular destinations from Chicago

From Chicago to Miami from $30
Price found 5 days ago

From Chicago to Detroit from $46
Price found 6 days ago

From Chicago to Managua from $114
Price found 2 days ago

From Chicago to Mexico City from $128
Price found 17 hours ago

See more routes

Last offers from Chicago

From - Destination Airlines Date Price
Chicago (MDW)
Miami (MIA)
Frontier 30 July $30

5 days ago

Chicago (MDW)
Acapulco de Juárez (ACA)
Frontier 21 May $198

20 hours ago

Chicago (MDW)
Miami (MIA)
Frontier 21 June $83

6 days ago

Last offers from Chicago round trip

From - Destination Airlines Go - Return Price
Chicago (MDW)
Oklahoma City (OKC)
Frontier 20 May
27 May
$264

26 hours ago

Chicago (MDW)
Guadalajara (GDL)
Volaris
Frontier
28 September
6 October
$263

25 hours ago

Chicago (MDW)
Guadalajara (GDL)
Volaris
Frontier
28 September
6 October
$263

25 hours ago

Chicago (MDW)
Guadalajara (GDL)
Volaris
Frontier
28 September
6 October
$282

25 hours ago

Chicago (MDW)
Guadalajara (GDL)
Volaris
VivaAerobus
28 September
6 October
$288

25 hours ago

Chicago (MDW)
Guadalajara (GDL)
Volaris
VivaAerobus
28 September
6 October
$306

25 hours ago

Chicago (MDW)
Guadalajara (GDL)
Volaris 28 September
6 October
$311

25 hours ago

Cheapest airlines in Chicago

Code Airline % Searches % being the cheapest
Y4 Volaris 47.6 80.0
PD Porter 2.5 76.7
F9 Frontier 23.6 66.6
SK SAS 1.4 59.1
WN Southwest Airlines 6.8 50.9
NK Spirit Airlines 12.7 50.8
CM Copa 1.3 36.9
KL KLM 10.3 31.4
VB VivaAerobus 4.0 26.2
TP TAP 3.2 26.2
Overall ranking and explanation

Frequently asked questions about flights from Chicago

How many airports are there in Chicago?

The closest airports to the city center are Midway, O'Hare, Chicago Executive, DuPage, Porter County Regional and Michigan City Municipal.

What is the cheapest month to fly from Chicago?

The cheapest month to fly from Chicago is November.
$0$1,000$2,000$405Jan$498Feb$333Mar$361Apr$277May$1,512Jun$387Jul$406Aug$474Sep$209Oct$162Nov$828Dec

In which month do plane tickets from Chicago reach higher prices?

The most expensive time to fly from Chicago is June.

What is the day of the week when flights from Chicago have the lowest prices?

The cheapest day of the week to fly from Chicago is Monday.
$400$600$800$724Sunday$416Monday$640Tuesday$570Wednesday$671Thursday$536Friday$471Saturday

How far in advance is it advisable to book a flight from Chicago?

Booking 80 days before you get the best price from Chicago.

Which airline offers the cheapest prices to fly from Chicago?

The cheapest prices from Chicago are usually offered by Volaris.

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