$105 Find Cheap Flights from Milwaukee to Chicago - Compare and Save

These are the earliest and latest flight times available from Milwaukee to Chicago:

• Earliest: departs at 5:00 am and lands at 6:14 am
• Latest: departs at 8:14 pm and lands at 9:28 pm.

The flight takes about 1h 14m.

Only Economy Class is available on flights from Milwaukee to Chicago.

A nonstop flight from Milwaukee to Chicago takes 1h 14m, covering 75 miles.

No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

Round-trip flights from Milwaukee to Chicago range from $197 to $261, with an average of $205 over the past 12 months. Anything below $197 counts as a good deal.

United Airlines is slightly above the route average for timely arrivals, while American Airlines has a lower on-time arrival rate. On-time arrival rates on Milwaukee to Chicago flights are:

• United Airlines: 89% on time
• American Airlines: 86% on time
• Southwest: 77% on time

Overall, flights on this route are punctual 86% of the time on average.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

Morning is the busiest departure period on Milwaukee to Chicago flights, with 59% of flights leaving in that window. Afternoon departures account for 30%, evening flights for 11%, and night flights for 0%.

Based on prices from the last 5 days, flying between Milwaukee and Chicago is around $209 round-trip, with a flight time of about 50m. Recent bus fares are around $37, with a trip time of about 2h 15m. Compared with flying, recent bus fares are roughly 83% lower. However, taking the bus takes about 1+ hours longer each way.

One-way fares from Milwaukee to Chicago are currently lower than usual. Average one-way flight prices are about $105, which is 49% below the typical average for this route.

Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

• Routes Car & Truck Rentals
• Europcar
• Hertz
• Dollar
• Ace

Near Chicago Midway Airport (MDW) — daily rates from around $32:

• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

• Alamo
• Enterprise Rent-A-Car
• Budget
• Avis
• National

Flights from Milwaukee to Chicago usually depart from Milwaukee-Mitchell (MKE) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

Night flights have the fewest delays on this route, while afternoon departures tend to have the most.

A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Milwaukee to Chicago route, 14% of flights were delayed in the past 3 months, with delays averaging 1h 58m.

Yes. Flexible dates can save you up to 32% on flights from Milwaukee to Chicago. Thursday is the cheapest departure day at $201 round-trip on average, while Saturday is the most expensive at $293, a difference of $92.

KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

3 airlines operate flights between Milwaukee and Chicago. The airlines offering nonstop flights on this route include:

• United Airlines
• American Airlines
• Southwest

Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago on KAYAK.

Among airlines operating Milwaukee to Chicago flights:

• United Airlines: offers extra legroom; offers free seat selection
• Southwest: offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

Here are some options for this route, based on selected ticket types and cabin classes:

• United Airlines: a cabin bag and a checked bag in Economy Class
• American Airlines: a cabin bag in Economy Class class
• Southwest: a cabin bag in Economy Class class

Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.