Cheap flights from Milwaukee to Chicago

One-way fares from $161 · MKE → CHI · prices found by travellers in the last 48 hours

Compare all dates Chicago → Milwaukee
Cheapest fare
$161

American Airlines · Sun, Nov 15

Cheapest month
November

from $161

Direct flights
Yes

American Airlines

Flight time
1h 15m

130 km

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Cheapest month to fly from Milwaukee to Chicago

Lowest one-way fare per person in each month. Choose a month to see every date.

  1. November 2026 Cheapest $161

Cheapest dates in November 2026

The lowest fares we've seen for each day, cheapest first.

American Airlines
Depart11:38 Sun, Nov 15MKE → ORD 1h 16m · Direct
$161one way, per person
View deal
American Airlines
Depart05:04 Mon, Nov 16MKE → ORD 1h 20m · Direct
$164one way, per person
View deal
See every date in November 2026 →

Plan the rest of your trip to Chicago

Where to stay, what to do and getting around, from our travel partners.

Where to stay

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Things to do

Things to do in ChicagoTours, attractions and day trips on Klook Explore →

Getting around

Airport transfer in ChicagoPre-book a driver to meet you at arrivals, with Kiwitaxi Book a transfer → Car hire in ChicagoCompare rental cars from major brands on EconomyBookings Compare cars →

About flights from Milwaukee to Chicago

Milwaukee (MKE) and Chicago (CHI) are about 130 km apart. Direct flights take around 1h 15m, and recent direct fares were with American Airlines. Over the next few months, one-way fares start from $161, and November 2026 is currently the cheapest month to fly.

These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.

Frequently asked questions

How much is a flight from Milwaukee to Chicago?

The cheapest one-way fare we've seen recently is $161 with American Airlines, departing Sunday, November 15, 2026.

What is the cheapest month to fly from Milwaukee to Chicago?

November 2026 currently has the lowest fares, from $161 one way.

Are there direct flights from Milwaukee to Chicago?

Yes. Recent direct fares were with American Airlines.

How long is the flight from Milwaukee to Chicago?

A direct flight takes about 1h 15m. Milwaukee and Chicago are around 130 km apart.

Which airlines fly from Milwaukee to Chicago?

Recent fares on this route were with American Airlines.

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