Cheap flights from Milwaukee to Chicago

General Mitchell
MKE
Chicago FSS
CHI

Flight deals from Milwaukee to Chicago

Below you can see the best deals on flights Milwaukee — Chicago for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 13 October, from $93.

Top 10 cheap flights from Milwaukee to Chicago

UA
$ 120

Milwaukee — Chicago

05:00—06:10
5 Sep 2026
1 h 10 m
Direct flight
UA
$ 120

Milwaukee — Chicago

10:19—11:30
5 Sep 2026
1 h 11 m
Direct flight
UA
$ 120

Milwaukee — Chicago

06:15—07:26
5 Sep 2026
1 h 11 m
Direct flight
UA
$ 120

Milwaukee — Chicago

07:18—08:29
5 Sep 2026
1 h 11 m
Direct flight
UA
$ 120

Milwaukee — Chicago

11:18—12:29
5 Sep 2026
1 h 11 m
Direct flight
UA
$ 120

Milwaukee — Chicago

13:19—14:30
5 Sep 2026
1 h 11 m
Direct flight
UA
$ 120

Milwaukee — Chicago

15:15—16:26
5 Sep 2026
1 h 11 m
Direct flight
UA
$ 120

Milwaukee — Chicago

17:17—18:30
5 Sep 2026
1 h 13 m
Direct flight
UA
$ 120

Milwaukee — Chicago

05:00—06:10
12 Sep 2026
1 h 10 m
Direct flight
UA
$ 120

Milwaukee — Chicago

12:05—13:15
12 Sep 2026
1 h 10 m
Direct flight

Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the Milwaukee — Chicago flight

Looking for cheap flights from Milwaukee to Chicago? Compare fares from different airlines, check the flight schedule and travel time — and book your Milwaukee — Chicago ticket online at the best price.

The route has direct flights — around 234 flights per week, flights are operated by United Airlines, American Airlines, Alaska Airlines, Air Canada and 3 more airlines, a nonstop flight takes about 59 min, the distance between the cities is around 131 km.

Planning your trip? You may find our Chicago travel guide, how to get from the airport into town and Chicago weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

Facts about this route

from $93Min. price
OctoberCheapest
AugustPeak season
YesDirect flights
131 kmDistance
59 minTravel time
7Airlines
234 / wkFlights

Flight schedule from Milwaukee to Chicago

The table shows direct flights from Milwaukee to Chicago on the selected date. The flight takes approximately 59 min. Regular flights are operated by United Airlines, American Airlines, Alaska Airlines and Air Canada. Departures from General Mitchell International Airport airports, arrivals at O'Hare International Airport, Chicago Midway International Airport and Midway International Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

Today
Any time
Last update: 15 Aug 2026

Flight ticket prices by day: Milwaukee — Chicago

Below is a calendar of the lowest flight ticket prices for Milwaukee — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $93 in October, and the most expensive are around $177 in August. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
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Prices by month

Average one-way fares from Milwaukee to Chicago by month. Tickets are usually cheapest in January (around $174) and priciest in July (about $242) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$174lowMay$230highSep$185low
Feb$179lowJun$236highOct$195medium
Mar$226highJul$242highNov$185low
Apr$205mediumAug$221mediumDec$236high

Some values are estimated based on seasonality.

When to fly

Weather in Chicago: it is warmest in July (up to 27 °C on average) and coolest in January (around 0 °C). The driest month is November.

Tickets are usually cheapest in October and most expensive in August. Compare prices and weather by month in the charts below to pick the best time to fly.

Temperature · Chicago

Dry and wet days · Chicago

Wind speed and direction · Chicago

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How to get the best deal on a Milwaukee — Chicago ticket

  • Book ahead: fares for Milwaukee — Chicago are usually lower 3–8 weeks before departure than at the last minute.
  • Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
  • The cheapest month to fly to Chicago is usually October — plan your trip around it if your dates are flexible.
  • Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
  • Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
  • Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
  • Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Airlines

Flights on the Milwaukee — Chicago route are operated by 7 airlines; United Airlines runs the most flights (around 60% of all flights). Compare carriers, flight shares and schedules below.

  • United AirlinesUA
    47x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight MKE → ORD47x/week
      Duration
      1h 10m
      Days
      MTWTFSS
    60.3%Open →
  • American AirlinesAA
    27x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight MKE → ORD27x/week
      Duration
      1h 19m
      Days
      MTWTFSS
    34.2%Open →
  • Alaska AirlinesAS
    3x/week
    WebsiteFleet: 31545M pax/year
    • Direct flight MKE → ORD3x/week
      Duration
      1h 3m
      Days
      MTWTFSS
    3.4%Open →
  • Air CanadaAC
    1x/week
    WebsiteFleet: 20346M pax/year
    • Direct flight MKE → ORD1x/week
    0.9%Open →
  • British AirwaysBA
    1x/week
    WebsiteFleet: 29243M pax/year
    • Direct flight MKE → ORD1x/week
    0.4%Open →
  • IberiaIB
    1x/week
    WebsiteFleet: 9224M pax/year
    • Direct flight MKE → ORD1x/week
    0.4%Open →
  • Japan AirlinesJL
    1x/week
    WebsiteFleet: 14540M pax/year
    • Direct flight MKE → ORD1x/week
      Duration
      1h 3m
      Days
      MTWTFSS
    0.4%Open →

Cities and airports on the Milwaukee — Chicago route

Flights Milwaukee — Chicago depart from General Mitchell International Airport and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Milwaukee

MKE
United States
About the cityHow to get thereWeatherAll about the country United States
Arrival

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Departure airports
Arrival airports

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Frequently asked questions about the Milwaukee — Chicago flight

How long is the flight from Milwaukee to Chicago?

A nonstop Milwaukee — Chicago flight takes about 59 min — the distance between the cities is around 131 km.

How far is it from Milwaukee to Chicago?

The distance from Milwaukee to Chicago is about 131 km, which a nonstop flight covers in around 59 min.

Are there direct flights from Milwaukee to Chicago?

Yes, there are nonstop flights Milwaukee — Chicago — around 234 flights per week.

Which airlines fly from Milwaukee to Chicago?

Airlines operating Milwaukee — Chicago include United Airlines, American Airlines, Alaska Airlines, Air Canada, British Airways. See the full list with schedules in the "Airlines" section on this page.

Which airports do Milwaukee — Chicago flights use?

Flights from Milwaukee depart from General Mitchell International Airport, and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from Milwaukee to Chicago?

The price of a Milwaukee — Chicago ticket depends on your travel date, season and demand: it is usually cheapest to fly in October, and most expensive in August. Tickets typically cost between $93 and $177. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights Milwaukee — Chicago?

Flights Milwaukee — Chicago are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is October. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from Milwaukee to Chicago?

To catch a low fare Milwaukee — Chicago, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually October.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.

Where else you can fly from Milwaukee

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New York CityMinneapolisAtlantaDetroitDenverSeattlePhiladelphiaOrlandoHoustonCharlotteDallasWashington, D.C.BostonPhoenixSalt Lake CityCancunFort MyersTampaLas VegasPunta Cana

Where else you can fly from Chicago

See all
New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverNashvilleLondonIndianapolisSan DiegoMontrealSt. LouisCharlottePhiladelphiaColumbusKansas CityPhoenixMiamiLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochesterCleveland

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