On this page, you can book flights from Milwaukee to Chicago. The 131-km route is highly frequented, with about 78 flights per week, making it easy to find a convenient departure time.
Flights are operated by airlines such as United Airlines, American Airlines, and Alaska Airlines. Before booking, check out the low-price calendar and the price trend chart, as well as information on how to get to the airport in Milwaukee and travel from the airport to downtown Chicago.
The table shows direct flights Milwaukee → 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.
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 AED 365 in e, and the most expensive are around AED 521 in J. 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.
Milwaukee → Chicago, average one-way price
| Month | Average price | Level | Month | Average price | Level | Month | Average price | Level |
|---|---|---|---|---|---|---|---|---|
| Jan | AED 687 | low | May | AED 907 | high | Sep | AED 727 | low |
| Feb | AED 705 | low | Jun | AED 929 | high | Oct | AED 767 | medium |
| Mar | AED 889 | high | Jul | AED 951 | high | Nov | AED 727 | low |
| Apr | AED 808 | medium | Aug | AED 871 | medium | Dec | AED 929 | high |
Some values are estimated based on seasonality.
Weather conditions in Chicago are most comfortable in July, when average temperatures reach 26.5°C. The coldest month is January, with temperatures dropping to -5°C, while the peak for precipitation and rainy days occurs in May and October.
The lowest flight prices are recorded in October, starting AED 365. The highest fares are typically seen in January, when ticket prices start AED 521, making it the least budget-friendly month to book.
For your trip, we recommend choosing August or September: the weather remains warm, and prices stay affordable, starting AED 386. It’s best to avoid the winter months due to the combination of cold weather and seasonal price hikes.
Seven airlines operate on the Milwaukee–Chicago route, with United Airlines and American Airlines leading in flight frequency. Most flights are direct, keeping travel time between the cities to a minimum. You can check the current schedule for specific days of the week in the interactive list below.
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.
With a distance of 131 km, the actual flight time is about 25–30 minutes; however, the total travel time, including taxiing, usually takes around 1 hour.
Regular service is provided by 7 carriers, including United Airlines, American Airlines, and Alaska Airlines.
Yes, due to the short distance, most flights between Milwaukee and Chicago are non-stop.
Ticket prices fluctuate constantly based on flight capacity. You can always check the current minimum—for example, starting from 7,734 ₽—in the low-price calendar on this page.
Most flights from Milwaukee arrive at Chicago O'Hare International Airport (ORD), the primary hub for the region.
Where travelers fly most — pick a route and check prices
