Find Cheap Flights from Milwaukee to Chicago (MKE - CHI)

Flights overview

Useful information for finding cheap flights from Milwaukee to Chicago and booking your next trip

Cheapest round-trip flights	$201	Southwest Nonstop 1 hr Thu, May 28 — Mon, Jun 1	The cheapest round-trip flight from Milwaukee to Chicago is currently $201
Cheapest one-way flight	$91	Southwest Nonstop 1 hr Wed, May 27	The cheapest one-way flight from Milwaukee to Chicago is currently $91
Last-minute weekend getaway	$424	Southwest Nonstop 1 hr Sat, May 9 — Sun, May 10	The cheapest last-minute weekend getaway from Milwaukee to Chicago is currently $424
Cheapest business class flights	$363	American Nonstop 2 hr Thu, May 28 — Mon, Jun 1	The cheapest business class round-trip flight from Milwaukee to Chicago is currently $363

Fastest flight	45 min	The fastest nonstop flight from Milwaukee to Chicago takes 45 min
Nonstop flights	Every day	There are direct flights on this route every day.

When is the cheapest time to fly?

The cheapest month to fly from Milwaukee to Chicago is typically January. The most expensive month to fly is typically May.

January Cheapest	Typical prices: $175–240
May Most expensive	Typical prices: $190–250

Popular airlines from Milwaukee to Chicago

United

Nonstop

from $210

Typical price: $175–235

65 weekly nonstop flights

MKE - ORD Every day

171 weekly connecting flights

MKE - ORD Every day
Southwest

Nonstop

from $201

Typical price: $215–490

14 weekly nonstop flights

MKE - MDW Every day

2566 weekly connecting flights

MKE - MDW, ORD Every day
American

Nonstop

from $201

Typical price: $175–250

58 weekly nonstop flights

MKE - ORD Every day

243 weekly connecting flights

MKE - ORD Every day
Alaska

from $771

Typical price: $550–1,250

21 weekly connecting flights

MKE - ORD Every day
Frontier

Typical price: $180–435

17 weekly connecting flights

MKE - MDW, ORD Every Mon, Wed, Thu, Fri, Sun
JetBlue

7 weekly connecting flights

MKE - ORD Every day

Popular airports near Milwaukee

Milwaukee Mitchell International Airport (MKE)

Milwaukee United States 14 min 6 mi
Chicago O'Hare International Airport (ORD)

Chicago United States 1 hr 15 min 73 mi
Chicago Midway International Airport (MDW)

Chicago United States 1 hr 46 min 87 mi
Dane County Regional Airport (MSN)

Madison United States 1 hr 17 min 72 mi

Popular airports near Chicago

Chicago O'Hare International Airport (ORD)

Chicago United States 26 min 16 mi
Chicago Midway International Airport (MDW)

Chicago United States 25 min 9 mi
Milwaukee Mitchell International Airport (MKE)

Milwaukee United States 1 hr 23 min 75 mi
Indianapolis International Airport (IND)

Indianapolis United States 2 hr 58 min 165 mi

Frequently asked questions about flying from Milwaukee to Chicago

The cheapest flights from Milwaukee to Chicago are usually in January. Typical ticket prices in January range from $175 to $240.

The cheapest round-trip flight from Milwaukee to Chicago recently found on Google Flights was with Southwest from $201. The cheapest one-way flight was with Southwest from $91.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest United flight from Milwaukee to Chicago is $210, flying from May 28 to May 31.
The cheapest Southwest flight from Milwaukee to Chicago is $201, flying from May 28 to Jun 1.
The cheapest American flight from Milwaukee to Chicago is $201, flying from May 28 to Jun 1.
The cheapest Alaska flight from Milwaukee to Chicago is $771, flying from May 28 to May 31.

The cheapest round-trip flight from Milwaukee to Chicago starts at $201 from Thu, May 28 to Mon, Jun 1. The cheapest one-way flight starts at $91 and departs on Wed, May 27.

45 min is the shortest flight time from Milwaukee to Chicago.

Chicago's peak season is Jun–Aug. Popular events throughout year include St. Patrick's Day, when the river is tinted green (Mar 17); the Pride Parade (Jun); the Taste of Chicago culinary festival (Jul) and the Jazz Festival (Sep). During the holiday season (Nov–Dec), the Magnificent Mile Lights Festival and Christkindlmarket, a German Christmas market in Daley Plaza, draw crowds to the city.

It's easy to use Google Flights to find the cheapest days to fly from Milwaukee to Chicago.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.

What counts as the best airline for your flights from Milwaukee to Chicago really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Milwaukee to Chicago.

In terms of nonstop flights, United is the most popular. United offers 65 nonstop flights and 171 connecting flights per week. United flies from Milwaukee Mitchell International Airport (MKE) to Chicago O'Hare International Airport (ORD) .

In terms of flights, Southwest is the most popular. Southwest offers 14 nonstop flights and 2,566 connecting flights per week. Southwest flies from Milwaukee Mitchell International Airport (MKE) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .

Other popular airlines flying from Milwaukee to Chicago are:

American offers 58 nonstop flights and 243 connecting flights per week. American flies from Milwaukee Mitchell International Airport (MKE) to Chicago O'Hare International Airport (ORD) .
Alaska offers 21 connecting flights per week. Alaska flies from Milwaukee Mitchell International Airport (MKE) to Chicago O'Hare International Airport (ORD) .
Frontier offers 17 connecting flights per week. Frontier flies from Milwaukee Mitchell International Airport (MKE) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
JetBlue offers 7 connecting flights per week. JetBlue flies from Milwaukee Mitchell International Airport (MKE) to Chicago O'Hare International Airport (ORD) .

The number of connecting flights refers to distinct flights with at least one stop between Milwaukee and Chicago.

The cheapest round-trip flight from Milwaukee to Chicago recently found on Google Flights was with Southwest from $201. The cheapest one-way flight was with Southwest from $91.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest United flight from Milwaukee to Chicago is $210, flying from May 28 to May 31.
The cheapest Southwest flight from Milwaukee to Chicago is $201, flying from May 28 to Jun 1.
The cheapest American flight from Milwaukee to Chicago is $201, flying from May 28 to Jun 1.
The cheapest Alaska flight from Milwaukee to Chicago is $771, flying from May 28 to May 31.

Southwest, United and American fly direct from Milwaukee to Chicago.

There are 65 United direct flights from Milwaukee to Chicago per week. Flights are available every day.
There are 14 Southwest direct flights from Milwaukee to Chicago per week. Flights are available every day.
There are 58 American direct flights from Milwaukee to Chicago per week. Flights are available every day.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

The cheapest last-minute deal between Milwaukee and Chicago at price $424 is offered by Southwest from Sat, May 9 to Sun, May 10.

Southwest, United and American fly direct from Milwaukee to Chicago.

There are 65 United direct flights from Milwaukee to Chicago per week. Flights are available every day.
There are 14 Southwest direct flights from Milwaukee to Chicago per week. Flights are available every day.
There are 58 American direct flights from Milwaukee to Chicago per week. Flights are available every day.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

There are direct flights from Milwaukee to Chicago on a daily basis.

The cheapest direct (nonstop) round-trip flights between Milwaukee and Chicago start at $201 from Thu, May 28 to Mon, Jun 1 with Southwest.

It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Milwaukee to Chicago, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.

The cheapest business class round-trip flights between Milwaukee and Chicago start at $363 from Thu, May 28 to Mon, Jun 1 with American.

The cheapest economy class round-trip flights between Milwaukee and Chicago start at $201 from Thu, May 28 to Mon, Jun 1.

To book business class trips from Milwaukee to Chicago, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.

The best last-minute getaway deal for the next weekend between Milwaukee and Chicago starts at $424 from Sat, May 9 to Sun, May 10 with Southwest.

The cheapest last-minute deal between Milwaukee and Chicago at price $424 is offered by Southwest from Sat, May 9 to Sun, May 10.

To find last-minute flight deals from Milwaukee to Chicago, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.