Cheap flights from Milwaukee to Chicago
Flights overview
Prices shown are for one adult in Economy class flights from Zürich to New York. This includes the cheapest Business class options where available.
Prices reflect the lowest available in the next three months, though they are subject to change and availability.
Last-minute deals apply to the cheapest weekend trips available in the next seven days, with weekend trips being flights departing between Thursday and Saturday and returning on Sunday or Monday.
Flight duration shown is based on nonstop flights or those with the fewest stops available.
Prices reflect the lowest available in the next three months, though they are subject to change and availability.
Last-minute deals apply to the cheapest weekend trips available in the next seven days, with weekend trips being flights departing between Thursday and Saturday and returning on Sunday or Monday.
Flight duration shown is based on nonstop flights or those with the fewest stops available.
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?
Typical prices for the least expensive flights for weekend trips from Milwaukee to Chicago per month. Insights are based on fares observed in the last 12 months. Current prices may differ.
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
Popularity is based on the number of weekly nonstop and connecting flights the airline operates. Connecting flights do not include interline routes.
Flight suggestions are based on an airline's cheapest round-trip fares from Milwaukee to Chicago in the next 3 months. Prices include required taxes + fees for one adult. Optional charges and bag fees may apply.
Typical prices are based on fares observed in the past year for one-week round trips with the same origin, destination, and airline.
- UnitedNonstopfrom $210Typical price: $175–23565 weekly nonstop flightsMKE - ORD Every day171 weekly connecting flightsMKE - ORD Every day
- SouthwestNonstopfrom $201Typical price: $215–49014 weekly nonstop flightsMKE - MDW Every day2566 weekly connecting flightsMKE - MDW, ORD Every day
- AmericanNonstopfrom $201Typical price: $175–25058 weekly nonstop flightsMKE - ORD Every day243 weekly connecting flightsMKE - ORD Every day
- Alaskafrom $771Typical price: $550–1,25021 weekly connecting flightsMKE - ORD Every day
- FrontierTypical price: $180–43517 weekly connecting flightsMKE - MDW, ORD Every Mon, Wed, Thu, Fri, Sun
- JetBlue7 weekly connecting flightsMKE - ORD Every day
Popular airports near Milwaukee
Distance and driving time are relative to the city center. Airports are listed based on distance from Milwaukee center and popularity with travelers.
- 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
Distance and driving time are relative to the city center. Airports are listed based on distance from Chicago center and popularity with travelers.
- 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:
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.
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:
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 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:
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.
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.
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.
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.
You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.
Search more flights
Popular trips from Milwaukee
These suggestions are based on the cheapest fares to popular destinations in the next six months.
Prices include required taxes + fees for 1 adult. Optional charges and bag fees may apply.
-
Las Vegas$289Jun 4 — Jun 81 stop 7 hr 3 min United
-
Paris$943Oct 30 — Nov 12 stops 12 hr 16 min Air France, Delta
-
Orlando$108May 28 — May 31Nonstop 2 hr 49 min Frontier
-
Seattle$329May 28 — Jun 11 stop 6 hr 40 min United
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