$100 Cheap Flights from Milwaukee (MKE) to Chicago (ORD)

View $100 flight on Sat, Nov 1, 2025Opens in a new window

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

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Cheap Flights from Milwaukee to Chicago (MKE-ORD)

Prices were available within the past 7 days and start at $100 for one-way flights and $179 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Wed, Oct 1 - Sun, Oct 5
MKE
Milwaukee
ORD
Chicago
$179 Roundtrip, found 3 hours ago
$179
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Wed, Oct 1 from Milwaukee to Chicago, returning Sun, Oct 5, priced at $179 found 3 hours ago
United
Thu, Sep 18 - Sun, Sep 21
MKE
Milwaukee
ORD
Chicago
$179 Roundtrip, found 3 hours ago
$179
Roundtrip
found 3 hours ago
Select United flight, departing Thu, Sep 18 from Milwaukee to Chicago, returning Sun, Sep 21, priced at $179 found 3 hours ago
United
Thu, Oct 9 - Sun, Oct 12
MKE
Milwaukee
ORD
Chicago
$184 Roundtrip, found 7 hours ago
$184
Roundtrip
found 7 hours ago
Select United flight, departing Thu, Oct 9 from Milwaukee to Chicago, returning Sun, Oct 12, priced at $184 found 7 hours ago
United
Thu, Sep 4 - Wed, Sep 10
MKE
Milwaukee
ORD
Chicago
$184 Roundtrip, just found
$184
Roundtrip
just found
Select United flight, departing Thu, Sep 4 from Milwaukee to Chicago, returning Wed, Sep 10, priced at $184 just found
Southwest Airlines
Fri, Sep 19 - Sun, Sep 21
MKE
Milwaukee
ORD
Chicago
$186 Roundtrip, found 8 hours ago
$186
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Fri, Sep 19 from Milwaukee to Chicago, returning Sun, Sep 21, priced at $186 found 8 hours ago
United
Mon, Sep 1 - Mon, Sep 8
MKE
Milwaukee
ORD
Chicago
$187 Roundtrip, found 11 hours ago
$187
Roundtrip
found 11 hours ago
Select United flight, departing Mon, Sep 1 from Milwaukee to Chicago, returning Mon, Sep 8, priced at $187 found 11 hours ago
United
Sat, Aug 30 - Sat, Sep 6
MKE
Milwaukee
ORD
Chicago
$188 Roundtrip, found 2 days ago
$188
Roundtrip
found 2 days ago
Select United flight, departing Sat, Aug 30 from Milwaukee to Chicago, returning Sat, Sep 6, priced at $188 found 2 days ago
United
Sat, Mar 28 - Fri, Apr 3
MKE
Milwaukee
ORD
Chicago
$189 Roundtrip, found 3 days ago
$189
Roundtrip
found 3 days ago
Select United flight, departing Sat, Mar 28 from Milwaukee to Chicago, returning Fri, Apr 3, priced at $189 found 3 days ago
JetBlue Airways
Mon, Sep 1 - Thu, Sep 4
MKE
Milwaukee
ORD
Chicago
$323 Roundtrip, found 1 day ago
$323
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Sep 1 from Milwaukee to Chicago, returning Thu, Sep 4, priced at $323 found 1 day ago
Delta
Tue, Sep 30 - Wed, Oct 22
MKE
Milwaukee
ORD
Chicago
$372 Roundtrip, found 1 day ago
$372
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 30 from Milwaukee to Chicago, returning Wed, Oct 22, priced at $372 found 1 day ago

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

March is typically the cheapest month to fly

From $179 - $349 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $608
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $608
Flights from Milwaukee (MKE) to Chicago (ORD)
Origin airport
General Mitchell Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, Southwest Airlines, United
Roundtrip price
$179
Distance
67 mi
Average flight time
1 hour 6 mins

Milwaukee to Chicago Flights

The cheapest times to fly from Milwaukee to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Milwaukee to Chicago are during the month of October. You can find some of the cheapest flights from Milwaukee to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Milwaukee to Chicago

Sunday is one of the best days to book for cheap flights from Milwaukee to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Milwaukee to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Milwaukee to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $100 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Milwaukee to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Milwaukee to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from General Mitchell Intl. Airport (MKE) to O'Hare Intl. Airport (ORD) cost?
Grab a cheap one-way flight from $100 or cheap return flight from $179 from General Mitchell Intl. Airport (MKE) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from General Mitchell Intl. Airport (MKE) to O'Hare Intl. Airport (ORD)?
The cheapest month to fly from MKE to ORD is October, when demand is low. Off-peak season is often when you'll find cheap fares for travel between these airports.
Which airlines fly direct from General Mitchell Intl. Airport (MKE) to O'Hare Intl. Airport (ORD)?
You can fly nonstop from General Mitchell Intl. Airport (MKE) to O'Hare Intl. Airport (ORD) on a United Airlines flight.
What is the cheapest airline that flies from General Mitchell Intl. Airport (MKE) to O'Hare Intl. Airport (ORD)?
The cheapest airline to offer flights between General Mitchell Intl. Airport (MKE) and O'Hare Intl. Airport (ORD) can change depending on when you want to travel. American Airlines and United Airlines are just some well-known options offering reasonable prices. Use Expedia's filter tool to compare airlines in one place and find the right MKE to ORD flight that fits your budget.
How many flights per day from General Mitchell Intl. Airport (MKE) to O'Hare Intl. Airport (ORD)?
With an average of 12 direct flights departing from General Mitchell Intl. Airport (MKE) to O'Hare Intl. Airport (ORD) each day, you'll be taking off on vacation soon enough.
What are the most popular departure times for flights from General Mitchell Intl. Airport (MKE) to O'Hare Intl. Airport (ORD)?
Flights between MKE and ORD are their busiest at 6 AM. If you're after a quieter trip and possibly cheaper fares, look for a departure that's outside typical rush times.
What day of the week has the most flights from MKE to ORD?
If you fly on a Friday, you'll get the widest range of choices for flights from General Mitchell Intl. Airport (MKE) to O'Hare Intl. Airport (ORD).
What is the earliest flight from General Mitchell Intl. Airport (MKE) to O'Hare Intl. Airport (ORD)?
General Mitchell Intl. Airport (MKE)'s first flight to O'Hare Intl. Airport (ORD) is at approximately 6:15AM UTC-6. With a travel duration of 1h 11m, you'll land at around 7:26AM UTC-6.
How long does it take to fly from General Mitchell Intl. Airport (MKE) to O'Hare Intl. Airport (ORD)?
It usually takes 1 hour and 11 minutes to travel the 65 mi from MKE to ORD.
What is the best time to fly from General Mitchell Intl. Airport (MKE) to O'Hare Intl. Airport (ORD)?
To avoid possible delays on the General Mitchell Intl. Airport (MKE) to O'Hare Intl. Airport (ORD) route, travel before 3 PM. Departures after this hour are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from General Mitchell Intl. Airport (MKE)?
If you're traveling on a direct flight from General Mitchell Intl. Airport (MKE) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from General Mitchell Intl. Airport (MKE) to O'Hare Intl. Airport (ORD) last-minute?
Holding off until right before your break to book your flight from MKE to ORD often results in higher prices. While you may find some last-minute discounts, they're not always guaranteed. Be flexible with your itinerary to maximize your chances of landing a bargain.
Is it cheaper to book a MKE to ORD flight and hotel package?
Opting for a MKE to ORD flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels in one place. Choose from our wide range of accommodations and then add flights, car rentals and activities to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from General Mitchell Intl. Airport (MKE) to O'Hare Intl. Airport (ORD)?
Typically, it's possible to cancel or reschedule your MKE to ORD flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find further details on our Customer Service portal.

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