$89+ Cheap flights from Chicago (CHI) to Milwaukee (MKE)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
Sep 5 — Sep 121
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Milwaukee with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Milwaukee
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Cheapest flights from Chicago to MilwaukeeExplore the most affordable flight options available from Chicago to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 6, 2026.
Explore the most affordable flight options available from Chicago to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 6, 2026.
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:45 pm -
Nonstop1h 10m
Sun 9/611:18 am -
Nonstop1h 11m
Deal found 8/5![United Airlines logo]()
$179
This Southwest deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:15 am -
Nonstop0h 50m
Sun 9/67:00 am -
Nonstop0h 50m
Deal found 8/6![Southwest logo]()
$179
This American Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:58 pm -
Nonstop1h 02m
Sun 9/66:00 am -
Nonstop1h 21m
Deal found 8/5![American Airlines logo]()
$180
This American Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/118:51 pm -
Nonstop1h 03m
Tue 9/228:31 am -
Nonstop1h 30m
Deal found 8/5![American Airlines logo]()
$189
This United Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:50 am -
Nonstop1h 10m
Fri 9/112:20 pm -
Nonstop1h 11m
Deal found 8/6![United Airlines logo]()
$197
This Southwest deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:40 pm -
Nonstop0h 45m
Fri 9/115:45 am -
Nonstop0h 45m
Deal found 8/6![Southwest logo]()
$197
This American Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:56 am -
Nonstop1h 05m
Sat 9/121:18 pm -
Nonstop1h 21m
Deal found 8/2![American Airlines logo]()
$199
This American Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:55 pm -
Nonstop1h 08m
Wed 9/238:14 pm -
Nonstop1h 16m
Deal found 8/2![American Airlines logo]()
$200
This United Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3011:41 am -
Nonstop0h 57m
Sun 9/611:18 am -
Nonstop1h 11m
Deal found 8/2![United Airlines logo]()
$204
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3010:25 am -
Nonstop0h 45m
Sun 9/67:00 am -
Nonstop0h 50m
Deal found 8/2![Southwest logo]()
$204
This United Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/142:04 pm -
Nonstop1h 07m
Fri 9/185:00 am -
Nonstop1h 11m
Deal found 8/2![United Airlines logo]()
$207
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:35 pm -
Nonstop0h 45m
Wed 9/238:20 am -
1 stop5h 35m
Deal found 8/2![Southwest logo]()
$209
Best flights from Chicago to MilwaukeeDiscover carefully curated flight deals from Chicago to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 6, 2026.
Discover carefully curated flight deals from Chicago to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 6, 2026.
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:45 pm -
Nonstop1h 10m
Sun 9/611:18 am -
Nonstop1h 11m
Deal found 8/5![United Airlines logo]()
$179
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:15 am -
Nonstop0h 50m
Sun 9/67:00 am -
Nonstop0h 50m
Deal found 8/4![Southwest logo]()
$179
This American Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:27 pm -
Nonstop1h 03m
Fri 9/118:31 am -
Nonstop1h 30m
Deal found 8/2![American Airlines logo]()
$189
This United Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:50 am -
Nonstop1h 10m
Fri 9/112:20 pm -
Nonstop1h 11m
Deal found 8/6![United Airlines logo]()
$197
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:40 pm -
Nonstop0h 45m
Sun 9/67:00 am -
Nonstop0h 50m
Deal found 8/2![Southwest logo]()
$197
This American Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:56 am -
Nonstop1h 05m
Sat 9/121:18 pm -
Nonstop1h 21m
Deal found 8/2![American Airlines logo]()
$199
This Southwest deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:40 pm -
Nonstop0h 45m
Fri 9/115:45 am -
Nonstop0h 45m
Deal found 8/6![Southwest logo]()
$197
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/14:05 pm -
Nonstop1h 10m
Tue 9/86:00 am -
Nonstop1h 11m
Deal found 8/4![United Airlines logo]()
$199
This American Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:55 pm -
Nonstop1h 08m
Wed 9/238:14 pm -
Nonstop1h 16m
Deal found 8/2![American Airlines logo]()
$200
This United Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/314:05 pm -
Nonstop1h 10m
Mon 9/710:19 am -
Nonstop1h 11m
Deal found 8/2![United Airlines logo]()
$199
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/28:40 pm -
Nonstop0h 45m
Thu 9/35:45 am -
Nonstop0h 45m
Deal found 8/4![Southwest logo]()
$199
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:45 pm -
Nonstop1h 10m
Wed 9/912:05 pm -
Nonstop1h 10m
Deal found 8/5![United Airlines logo]()
$199
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:10 pm -
Nonstop0h 55m
Sat 9/261:30 pm -
Nonstop0h 50m
Deal found 8/5![Southwest logo]()
$199
This United Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:59 am -
Nonstop1h 08m
Tue 10/65:00 am -
Nonstop1h 10m
Deal found 8/1![United Airlines logo]()
$199
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/34:05 pm -
Nonstop1h 10m
Thu 9/1010:30 am -
Nonstop1h 11m
Deal found 8/5![United Airlines logo]()
$199
Last-minute flights from Chicago to MilwaukeeDiscover last-minute flight deals from Chicago to Milwaukee. Data last updated August 6, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Milwaukee. Data last updated August 6, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3011:41 am -
Nonstop0h 57m
Sun 9/611:18 am -
Nonstop1h 11m
Deal found 8/2![United Airlines logo]()
$204
This United Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:50 am -
Nonstop1h 10m
Fri 9/112:20 pm -
Nonstop1h 11m
Deal found 8/6![United Airlines logo]()
$197
This Southwest deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:40 pm -
Nonstop0h 45m
Fri 9/115:45 am -
Nonstop0h 45m
Deal found 8/6![Southwest logo]()
$197
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:45 pm -
Nonstop1h 10m
Sun 9/611:18 am -
Nonstop1h 11m
Deal found 8/5![United Airlines logo]()
$179
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:15 am -
Nonstop0h 50m
Sun 9/67:00 am -
Nonstop0h 50m
Deal found 8/4![Southwest logo]()
$179
This American Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:58 pm -
Nonstop1h 02m
Sun 9/66:00 am -
Nonstop1h 21m
Deal found 8/5![American Airlines logo]()
$180
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/81:00 pm -
2 stops7h 35m
Fri 9/115:45 am -
Nonstop0h 45m
Deal found 8/1![Southwest logo]()
$204
This American Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/118:51 pm -
Nonstop1h 03m
Tue 9/228:31 am -
Nonstop1h 30m
Deal found 8/5![American Airlines logo]()
$189
This American Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:56 am -
Nonstop1h 05m
Sat 9/121:18 pm -
Nonstop1h 21m
Deal found 8/2![American Airlines logo]()
$199
This United Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/142:04 pm -
Nonstop1h 07m
Fri 9/185:00 am -
Nonstop1h 11m
Deal found 8/2![United Airlines logo]()
$207
This American Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:55 pm -
Nonstop1h 08m
Wed 9/238:14 pm -
Nonstop1h 16m
Deal found 8/2![American Airlines logo]()
$200
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:35 pm -
Nonstop0h 45m
Wed 9/238:20 am -
1 stop5h 35m
Deal found 8/2![Southwest logo]()
$209
One-way flights from Chicago to MilwaukeeSearch for one-way flight options from Chicago to Milwaukee. Find affordable one-way fares based on user searches. Data last updated August 6, 2026.
Search for one-way flight options from Chicago to Milwaukee. Find affordable one-way fares based on user searches. Data last updated August 6, 2026.
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:27 pm -
Nonstop1h 03m
Deal found 8/4![American Airlines logo]()
$89
This United Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:15 pm -
Nonstop1h 10m
Deal found 8/6![United Airlines logo]()
$90
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:15 am -
Nonstop0h 50m
Deal found 8/4![Southwest logo]()
$90
This American Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2911:50 am -
Nonstop0h 57m
Deal found 8/2![American Airlines logo]()
$100
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:40 pm -
Nonstop0h 45m
Deal found 8/2![Southwest logo]()
$100
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/184:20 pm -
Nonstop1h 10m
Deal found 8/4![United Airlines logo]()
$108
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/188:40 pm -
Nonstop0h 45m
Deal found 8/4![Southwest logo]()
$108
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/48:15 pm -
Nonstop1h 10m
Deal found 8/4![United Airlines logo]()
$115
This United Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/34:35 pm -
Nonstop1h 03m
Deal found 8/6![United Airlines logo]()
$135
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:00 pm -
2 stops7h 30m
Deal found 8/3![Southwest logo]()
$139
This United Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:50 am -
Nonstop1h 10m
Deal found 8/3![United Airlines logo]()
$143
This United Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/175:59 am -
Nonstop1h 08m
Deal found 8/2![United Airlines logo]()
$144
Find flight deals from Chicago to Milwaukee
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Milwaukee (MKE). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $179 (United Airlines) |
One-way from | $89 (American Airlines) |
Good round-trip deal | $179 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Milwaukee that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 6, 2026.
Use the filters below to find and compare flights from Chicago to Milwaukee that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMilwaukee
ORD Chicago O'Hare Intl - MKE Milwaukee-Mitchell
ORDMKE
Chicago O'Hare Intl
Sat 9/5
5:45 pm-6:55 pm
Nonstop1h 10m
Milwaukee-Mitchell
Sun 9/6
11:18 am-12:29 pm
Nonstop1h 11m
$179
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Sat 9/5
10:15 am-11:05 am
Nonstop0h 50m
Milwaukee-Mitchell
Sun 9/6
7:00 am-7:50 am
Nonstop0h 50m
$179
ChicagoMilwaukee
ORD Chicago O'Hare Intl - MKE Milwaukee-Mitchell
ORDMKE
Chicago O'Hare Intl
Tue 9/8
5:27 pm-6:30 pm
Nonstop1h 03m
Milwaukee-Mitchell
Fri 9/11
8:31 am-10:01 am
Nonstop1h 30m
$189
ChicagoMilwaukee
ORD Chicago O'Hare Intl - MKE Milwaukee-Mitchell
ORDMKE
Chicago O'Hare Intl
Fri 9/4
8:50 am-10:00 am
Nonstop1h 10m
Milwaukee-Mitchell
Fri 9/11
2:20 pm-3:31 pm
Nonstop1h 11m
$197
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Fri 9/4
8:40 pm-9:25 pm
Nonstop0h 45m
Milwaukee-Mitchell
Sun 9/6
7:00 am-7:50 am
Nonstop0h 50m
$197
Quickest round-trip
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Fri 9/4
8:40 pm-9:25 pm
Nonstop0h 45m
Milwaukee-Mitchell
Fri 9/11
5:45 am-6:30 am
Nonstop0h 45m
$197
ChicagoMilwaukee
ORD Chicago O'Hare Intl - MKE Milwaukee-Mitchell
ORDMKE
Chicago O'Hare Intl
Sat 9/12
6:56 am-8:01 am
Nonstop1h 05m
Milwaukee-Mitchell
Sat 9/12
1:18 pm-2:39 pm
Nonstop1h 21m
$199
ChicagoMilwaukee
ORD Chicago O'Hare Intl - MKE Milwaukee-Mitchell
ORDMKE
Chicago O'Hare Intl
Tue 9/1
4:05 pm-5:15 pm
Nonstop1h 10m
Milwaukee-Mitchell
Tue 9/8
6:00 am-7:11 am
Nonstop1h 11m
$199
ChicagoMilwaukee
ORD Chicago O'Hare Intl - MKE Milwaukee-Mitchell
ORDMKE
Chicago O'Hare Intl
Mon 8/31
4:05 pm-5:15 pm
Nonstop1h 10m
Milwaukee-Mitchell
Mon 9/7
10:19 am-11:30 am
Nonstop1h 11m
$199
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Wed 9/2
8:40 pm-9:25 pm
Nonstop0h 45m
Milwaukee-Mitchell
Thu 9/3
5:45 am-6:30 am
Nonstop0h 45m
$199
Showing 1-10 of 35 resultsSorted by cheapest first
Compare providers for flights from Chicago to Milwaukee
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Milwaukee in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Milwaukee flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Milwaukee flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Milwaukee flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Milwaukee flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Milwaukee flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to Milwaukee
Have a flexible travel schedule? Discover the best time to fly to Milwaukee from Chicago with our price prediction graph.
CHI-MKE
ORD-MKE
MDW-MKE
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Milwaukee
CHI-MKE
ORD-MKE
MDW-MKE
What is the cheapest time of day to fly from CHI to MKE?
Find hourly flight availability from Chicago to Milwaukee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 6, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 39% on flights from Chicago to Milwaukee by exploring options for tickets in the afternoon.
Weekly flight availability from Chicago to Milwaukee
Explore weekly flight availability from Chicago to Milwaukee. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 6, 2026.
The most flights from CHI to MKE are scheduled on a Tuesday (59 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (21 on average).
Related info for your journey
Find useful and relevant information for your journey from Chicago to Milwaukee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Milwaukee?
Book flights to Milwaukee if you plan to visit one of these locationsSheboygan
Port Washington
New Berlin
Oak Creek
Wauwatosa
Browse thousands of different options on Cheapflights for your next trip
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Complete your trip
Complete your trip to Milwaukee by adding a car rental and/or hotel reservation to your travel itinerary.
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Other flights to Milwaukee
Explore flights to Milwaukee departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 6, 2026.
Chicago and Milwaukee flights
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Top 2 airlines flying from Chicago to Milwaukee
Discover the top 2 airlines that operate flights from Chicago to Milwaukee. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$179 | Average$207 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$179 | Average$318 | FlexibilityNo cancel fee | On-time69% |