A spacious airport terminal with high ceilings, check-in counters, and a Starbucks coffee shop.

CA $121 Cheap Flights from Milwaukee (MKE) to Chicago (ORD)

View CA $121 flight on Wed, Jul 29, 2026Opens in a new window

Popular airlines from General Mitchell Intl. Airport (MKE) to Chicago O'Hare International Airport (ORD)

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 30% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap flights from Milwaukee (MKE) to Chicago (ORD)

Prices were available within the past 7 days and start at CA $121 for one-way flights and CA $242 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Wed, Jul 29 - Wed, Aug 5
MKE
Milwaukee
ORD
Chicago
CA $242 Roundtrip, found 4 days ago
CA $242
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Jul 29 from Milwaukee to Chicago, returning Wed, Aug 5, priced at CA $242 found 4 days ago
American Airlines
Wed, Jul 29 - Wed, Aug 5
MKE
Milwaukee
ORD
Chicago
CA $243 Roundtrip, found 4 days ago
CA $243
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Jul 29 from Milwaukee to Chicago, returning Wed, Aug 5, priced at CA $243 found 4 days ago
American Airlines
Wed, Jul 29 - Wed, Aug 5
MKE
Milwaukee
ORD
Chicago
CA $276 Roundtrip, found 4 days ago
CA $276
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Jul 29 from Milwaukee to Chicago, returning Wed, Aug 5, priced at CA $276 found 4 days ago
American Airlines
Wed, Jul 29 - Wed, Aug 5
MKE
Milwaukee
ORD
Chicago
CA $278 Roundtrip, found 4 days ago
CA $278
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Jul 29 from Milwaukee to Chicago, returning Wed, Aug 5, priced at CA $278 found 4 days ago
American Airlines
Wed, Jul 29 - Wed, Aug 5
MKE
Milwaukee
ORD
Chicago
CA $293 Roundtrip, found 4 days ago
CA $293
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Jul 29 from Milwaukee to Chicago, returning Wed, Aug 5, priced at CA $293 found 4 days ago
American Airlines
Wed, Jul 29 - Wed, Aug 5
MKE
Milwaukee
ORD
Chicago
CA $310 Roundtrip, found 4 days ago
CA $310
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Jul 29 from Milwaukee to Chicago, returning Wed, Aug 5, priced at CA $310 found 4 days ago
American Airlines
Wed, Jul 29 - Wed, Aug 5
MKE
Milwaukee
ORD
Chicago
CA $326 Roundtrip, found 4 days ago
CA $326
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Jul 29 from Milwaukee to Chicago, returning Wed, Aug 5, priced at CA $326 found 4 days ago
American Airlines
Wed, Jul 29 - Wed, Aug 5
MKE
Milwaukee
ORD
Chicago
CA $342 Roundtrip, found 4 days ago
CA $342
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Jul 29 from Milwaukee to Chicago, returning Wed, Aug 5, priced at CA $342 found 4 days ago
American Airlines
Wed, Jul 29 - Wed, Aug 5
MKE
Milwaukee
ORD
Chicago
CA $344 Roundtrip, found 4 days ago
CA $344
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Jul 29 from Milwaukee to Chicago, returning Wed, Aug 5, priced at CA $344 found 4 days ago
American Airlines
Wed, Jul 29 - Wed, Aug 5
MKE
Milwaukee
ORD
Chicago
CA $347 Roundtrip, found 4 days ago
CA $347
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Jul 29 from Milwaukee to Chicago, returning Wed, Aug 5, priced at CA $347 found 4 days ago

Frequently asked questions

Which airlines fly direct from Milwaukee, WI (MKE-General Mitchell Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Enter MKE to ORD and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
How do I find cheap flights from Milwaukee, WI (MKE-General Mitchell Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from Milwaukee, WI (MKE-General Mitchell Intl.) to Chicago, IL (ORD-O'Hare Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Milwaukee, WI (MKE-General Mitchell Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best airline to fly with from Milwaukee, WI (MKE-General Mitchell Intl.) (MKE) to Chicago, IL (ORD-O'Hare Intl.) (ORD) will differ from traveller to traveller. If you like to fly early, UA offers early morning flights. If price is the most important factor, UA typically offers the lowest fares. DL offers the most daily flights from Milwaukee, WI (MKE-General Mitchell Intl.) (MKE) to Chicago, IL (ORD-O'Hare Intl.) (ORD), which is brilliant if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Milwaukee, WI (MKE-General Mitchell Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Milwaukee, WI (MKE-General Mitchell Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
There are approximately 18 nonstop flights per day from Milwaukee, WI (MKE-General Mitchell Intl.) (MKE) to Chicago, IL (ORD-O'Hare Intl.) (ORD). For even more choice, look at flights that include layovers, as there are around 35 connecting flights per day. Some common connection points include Hartsfield-Jackson Atlanta Intl. (ATL), Minneapolis - St. Paul Intl. (MSP), and Detroit Metropolitan Wayne County (DTW).
What is the earliest flight from Milwaukee, WI (MKE-General Mitchell Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Milwaukee, WI (MKE-General Mitchell Intl.) to Chicago, IL (ORD-O'Hare Intl.) typically departs at approximately 5:00 AM local time, operated by American Airlines. This is a seasonal service active in February and March. An early departure like this can help you maximise your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Milwaukee, WI (MKE-General Mitchell Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
You'll typically find the most flights from Milwaukee, WI (MKE-General Mitchell Intl.) (MKE) to Chicago, IL (ORD-O'Hare Intl.) (ORD) on a Tuesday, with around 33 flights available. This gives you a good selection of options for your travel plans. Major airlines on this route include Delta Air Lines, United Airlines, and American Airlines. Flight schedules are consistent throughout the week, so you'll have plenty of options no matter when you choose to fly.
What are the most popular departure times for flights from Milwaukee, WI (MKE-General Mitchell Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from Milwaukee, WI (MKE-General Mitchell Intl.) to Chicago, IL (ORD-O'Hare Intl.) are in the early morning, from 6am to 9am. About 36% of passengers prefer this time. Many major carriers, including American Airlines, Delta Air Lines and United Airlines, offer flights during this window. This timing works well because it allows you to get an early start on your day in Chicago, whether for business or leisure.
How long does it take to fly from Milwaukee, WI (MKE-General Mitchell Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
A nonstop flight from MKE to ORD typically takes around 1 hour 20 minutes, covering approximately 67 miles. Connecting flights on this route usually add 5 hours 30 minutes to your travel time. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Milwaukee, WI (MKE-General Mitchell Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Select the "Business class" and "First class" filters when looking for MKE to ORD flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Milwaukee, WI (MKE-General Mitchell Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a Milwaukee, WI (MKE-General Mitchell Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from General Mitchell Intl. (MKE)?
From General Mitchell Intl. (MKE), you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW) in Chicago. Some flights may connect through major hubs like Charlotte-Douglas Intl. (CLT), Detroit Metropolitan Wayne County (DTW), Minneapolis - St. Paul Intl. (MSP) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Milwaukee, WI (MKE-General Mitchell Intl.) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from Milwaukee, WI (MKE-General Mitchell Intl.) to Chicago, IL (ORD-O'Hare Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Milwaukee, WI (MKE-General Mitchell Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a Milwaukee, WI (MKE-General Mitchell Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Milwaukee, WI (MKE-General Mitchell Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your Milwaukee, WI (MKE-General Mitchell Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
General Mitchell Intl.
Destination airport
O'Hare Intl.
Roundtrip price
CA $242
Distance
107 km
Average flight time
1 hour 8 mins

Book with confidence

Milwaukee to Chicago Flights

The easy way to book your flights from Milwaukee to Chicago 

With Expedia, it’s simple to find and book flights to Chicago from Milwaukee whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to O'Hare Intl., too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Milwaukee to Chicago today, tomorrow, or this week.  

 

Save dollars with cheap flights from General Mitchell Intl., MKE to O'Hare Intl., ORD 

Sort your search results by price to find great deals on your flight from Milwaukee to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Milwaukee currently is just CA $242 rising to CA $550.  

Here are more money-saving tips: 

  • Fly in July when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Chicago  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Chicago from Milwaukee 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today.

Milwaukee to Chicago Flights

Explore a world of travel with Expedia

*Available to Expedia members.