S$279 Cheap Flights from Chicago to Milwaukee

View S$279 flight on Mon, 22 Sep, 2025Opens in a new window

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

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 40% on select hotels after you book a flight*
  • payments icon
    Earn twice
    Earn your airline miles on top of our rewards
    Sign in

Cheap Flights from Chicago to Milwaukee (ORD-MKE)

Prices were available within the past 7 days and start at S$279 for one-way flights and S$305 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Wed, 6 Aug - Sat, 9 Aug
ORD
Chicago
MKE
Milwaukee
S$305 Return, found 1 day ago
S$305
Return
found 1 day ago
Select American Airlines flight, departing Wed, 6 Aug from Chicago to Milwaukee, returning Sat, 9 Aug, priced at S$305 found 1 day ago
United
Wed, 6 Aug - Sat, 9 Aug
ORD
Chicago
MKE
Milwaukee
S$305 Return, found 1 day ago
S$305
Return
found 1 day ago
Select United flight, departing Wed, 6 Aug from Chicago to Milwaukee, returning Sat, 9 Aug, priced at S$305 found 1 day ago
American Airlines
Thu, 14 Aug - Thu, 21 Aug
ORD
Chicago
MKE
Milwaukee
S$306 Return, found 2 days ago
S$306
Return
found 2 days ago
Select American Airlines flight, departing Thu, 14 Aug from Chicago to Milwaukee, returning Thu, 21 Aug, priced at S$306 found 2 days ago
United
Wed, 6 Aug - Sat, 9 Aug
ORD
Chicago
MKE
Milwaukee
S$325 Return, found 1 day ago
S$325
Return
found 1 day ago
Select United flight, departing Wed, 6 Aug from Chicago to Milwaukee, returning Sat, 9 Aug, priced at S$325 found 1 day ago
United
Thu, 14 Aug - Thu, 21 Aug
ORD
Chicago
MKE
Milwaukee
S$326 Return, found 2 days ago
S$326
Return
found 2 days ago
Select United flight, departing Thu, 14 Aug from Chicago to Milwaukee, returning Thu, 21 Aug, priced at S$326 found 2 days ago
American Airlines
Wed, 6 Aug - Sat, 9 Aug
ORD
Chicago
MKE
Milwaukee
S$339 Return, found 1 day ago
S$339
Return
found 1 day ago
Select American Airlines flight, departing Wed, 6 Aug from Chicago to Milwaukee, returning Sat, 9 Aug, priced at S$339 found 1 day ago
United
Wed, 6 Aug - Sat, 9 Aug
ORD
Chicago
MKE
Milwaukee
S$344 Return, found 1 day ago
S$344
Return
found 1 day ago
Select United flight, departing Wed, 6 Aug from Chicago to Milwaukee, returning Sat, 9 Aug, priced at S$344 found 1 day ago
American Airlines
Wed, 6 Aug - Sat, 9 Aug
ORD
Chicago
MKE
Milwaukee
S$351 Return, found 1 day ago
S$351
Return
found 1 day ago
Select American Airlines flight, departing Wed, 6 Aug from Chicago to Milwaukee, returning Sat, 9 Aug, priced at S$351 found 1 day ago
United
Wed, 6 Aug - Sat, 9 Aug
ORD
Chicago
MKE
Milwaukee
S$363 Return, found 1 day ago
S$363
Return
found 1 day ago
Select United flight, departing Wed, 6 Aug from Chicago to Milwaukee, returning Sat, 9 Aug, priced at S$363 found 1 day ago
Delta
Mon, 22 Sep - Fri, 26 Sep
ORD
Chicago
MKE
Milwaukee
S$1,156 Return, found 3 hours ago
S$1,156
Return
found 3 hours ago
Select Delta flight, departing Mon, 22 Sep from Chicago to Milwaukee, returning Fri, 26 Sep, priced at S$1,156 found 3 hours ago

Find the cheapest month to fly from Chicago (ORD) to Milwaukee (MKE)

February is typically the cheapest month to fly

From S$228 - S$472 per traveller.

Graph displaying average flight prices per month

0
Chicago to Milwaukee route information
Origin airport
O'Hare Intl.
Destination airport
General Mitchell Intl.
Airlines serving
American Airlines, United
Return price
S$305
Distance
107 km

Perfect flights from Chicago to Milwaukee

Your Journey from Chicago to Milwaukee

Start your unforgettable journey with Expedia. Our broad selection of flights from Chicago to Milwaukee caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including American Airlines, United, Delta. Our selection of flights from O'Hare Intl. to General Mitchell Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Chicago to Milwaukee Flights

Experience the joy of finding cheap flights from O'Hare Intl. to General Mitchell Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$279 and roundtrip prices from S$305*.
 

Pre-Flight Essentials

Ensure a smooth journey from Chicago to Milwaukee with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Milwaukee

Picture yourself stepping off the plane in Milwaukee and immersing yourself in the unique atmosphere of Milwaukee. From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Chicago to Milwaukee Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Chicago to Milwaukee.
 

Beyond the Flight – Exploring Milwaukee

With Expedia, your adventure extends beyond the flight. Explore Milwaukee at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Chicago to Milwaukee with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Chicago to Milwaukee with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Frequently asked questions

How much is a flight from O'Hare Airport to Mitchell Intl. Airport?
Based on airfares listed within the last 7 days on Expedia for flights departing within the next year, round-trip journeys between O'Hare Airport and Mitchell Intl. Airport start from S$305. Book ASAP to secure the best price for your journey. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from O'Hare Intl. Airport (ORD) to MKE?
This can differ between airlines, as each has its own terms and conditions. Head to the Customer Service Portal, where you'll find simple instructions on how to cancel your flight online.
How do I find cheap flights from O'Hare Intl. Airport (ORD) to General Mitchell Intl. Airport (MKE) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for O'Hare Intl. Airport (ORD) to General Mitchell Intl. Airport (MKE) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from O'Hare Airport to MKE?
That new movie you've been wanting to see will just have to wait --- the flight distance between O'Hare Airport (ORD) and MKE (MKE) is only 110 kilometres. The captain will be instructing you to put your seat upright for touchdown before you know it.
Which airlines fly direct from ORD to MKE?
United Airlines (UA) is a popular option. It operates 208 flights between O'Hare Intl. Airport (ORD) and Mitchell Intl. Airport each month. You could also check out the fares available with American Airlines (AA). This airline operates 91 flights every month between Chicago and Milwaukee.
Are ORD to MKE flight tickets cheaper when they're purchased at the last minute?
Fares from ORD to MKE are available up to 12 months before departure on Expedia. And although you may occasionally score great last-minute deal, it's not something you should bank on. Also, booking your flights ahead of time means you'll have more choices --- and you can avoid being wedged in the dreaded middle seat! We're always updating our fares to bring you the best bargains, so keep checking in for all the latest specials.

Explore a world of travel with Expedia

Chicago Airports

Chicago

*Available to Expedia members.