$93+ Cheap flights from Chicago (CHI) to Milwaukee (MKE)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
Nov 29 — Dec 61
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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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 October 30, 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 October 30, 2026.
This United Airlines deal was found by Cheapflights users on 10/27. 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 11/197:30 am -
Nonstop1h 06m
Mon 11/232:23 pm -
Nonstop1h 12m
Deal found 10/27![United Airlines logo]()
$185
This Southwest deal was found by Cheapflights users on 10/29. 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.
Thu 11/1910:10 am -
Nonstop0h 50m
Mon 11/234:50 pm -
Nonstop0h 50m
Deal found 10/29![Southwest logo]()
$185
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 11/196:56 pm -
Nonstop1h 04m
Mon 11/238:48 am -
Nonstop1h 27m
Deal found 10/28![American Airlines logo]()
$186
This United Airlines deal was found by Cheapflights users on 10/27. 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 12/46:29 am -
Nonstop1h 06m
Mon 12/72:38 pm -
Nonstop1h 12m
Deal found 10/27![United Airlines logo]()
$204
This United Airlines deal was found by Cheapflights users on 10/29. 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 11/279:20 pm -
Nonstop0h 55m
Fri 12/47:18 pm -
Nonstop1h 12m
Deal found 10/29![United Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 10/29. 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 11/279:15 pm -
Nonstop1h 00m
Fri 12/44:20 pm -
Nonstop0h 55m
Deal found 10/29![Southwest logo]()
$209
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Mon 12/146:44 pm -
Nonstop1h 16m
Mon 12/212:09 pm -
Nonstop1h 21m
Deal found 10/29![American Airlines logo]()
$210
This Southwest deal was found by Cheapflights users on 10/29. 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.
Thu 11/265:40 am -
1 stop5h 15m
Thu 12/38:00 am -
1 stop7h 30m
Deal found 10/29![Southwest logo]()
$210
This Southwest deal was found by Cheapflights users on 10/27. 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 12/119:15 pm -
Nonstop1h 00m
Fri 12/185:45 am -
Nonstop1h 00m
Deal found 10/27![Southwest logo]()
$223
This United Airlines deal was found by Cheapflights users on 10/26. 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 11/257:30 am -
Nonstop1h 06m
Sat 11/289:20 am -
Nonstop1h 10m
Deal found 10/26![United Airlines logo]()
$227
This Southwest deal was found by Cheapflights users on 10/26. 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 11/2510:00 am -
Nonstop0h 50m
Sat 11/285:40 am -
Nonstop1h 05m
Deal found 10/26![Southwest logo]()
$227
This United Airlines deal was found by Cheapflights users on 10/26. 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 12/195:45 pm -
Nonstop1h 11m
Sun 12/2010:38 am -
Nonstop1h 20m
Deal found 10/26![United Airlines logo]()
$245
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 October 30, 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 October 30, 2026.
This United Airlines deal was found by Cheapflights users on 10/27. 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 11/1910:25 am -
Nonstop1h 03m
Mon 11/238:00 am -
Nonstop1h 12m
Deal found 10/27![United Airlines logo]()
$185
This Southwest deal was found by Cheapflights users on 10/26. 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.
Thu 11/1910:10 am -
Nonstop0h 50m
Mon 11/234:50 pm -
Nonstop0h 50m
Deal found 10/26![Southwest logo]()
$185
This American Airlines deal was found by Cheapflights users on 10/27. 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 12/116:44 pm -
Nonstop1h 16m
Fri 12/185:00 am -
Nonstop1h 26m
Deal found 10/27![American Airlines logo]()
$275
This Southwest deal was found by Cheapflights users on 10/27. 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 11/249:30 pm -
Nonstop0h 55m
Tue 12/14:15 pm -
Nonstop0h 55m
Deal found 10/27![Southwest logo]()
$185
This United Airlines deal was found by Cheapflights users on 10/27. 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 12/46:29 am -
Nonstop1h 06m
Mon 12/72:38 pm -
Nonstop1h 12m
Deal found 10/27![United Airlines logo]()
$204
This United Airlines deal was found by Cheapflights users on 10/29. 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 11/279:20 pm -
Nonstop0h 55m
Fri 12/47:18 pm -
Nonstop1h 12m
Deal found 10/29![United Airlines logo]()
$209
This United Airlines deal was found by Cheapflights users on 10/26. 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 2/28:45 am -
Nonstop1h 15m
Sat 2/610:35 am -
Nonstop1h 20m
Deal found 10/26![United Airlines logo]()
$223
This United Airlines deal was found by Cheapflights users on 10/26. 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 11/257:30 am -
Nonstop1h 06m
Sat 11/289:20 am -
Nonstop1h 10m
Deal found 10/26![United Airlines logo]()
$227
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 11/129:35 pm -
Nonstop1h 02m
Mon 11/167:29 pm -
Nonstop1h 31m
Deal found 10/28![American Airlines logo]()
$327
This United Airlines deal was found by Cheapflights users on 10/25. 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 11/229:20 pm -
Nonstop0h 55m
Sun 11/296:47 am -
Nonstop1h 12m
Deal found 10/25![United Airlines logo]()
$268
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/169:20 pm -
Nonstop0h 55m
Thu 12/177:00 pm -
Nonstop1h 21m
Deal found 10/28![United Airlines logo]()
$275
Last-minute flights from Chicago to MilwaukeeDiscover last-minute flight deals from Chicago to Milwaukee. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Milwaukee. Data last updated October 30, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/27. 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.
Thu 11/126:49 am -
Nonstop0h 59m
Tue 11/172:55 pm -
Nonstop1h 15m
Deal found 10/27![American Airlines logo]()
$258
This United Airlines deal was found by Cheapflights users on 10/27. 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 11/197:30 am -
Nonstop1h 06m
Mon 11/232:23 pm -
Nonstop1h 12m
Deal found 10/27![United Airlines logo]()
$185
This Southwest deal was found by Cheapflights users on 10/29. 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.
Thu 11/1910:10 am -
Nonstop0h 50m
Mon 11/234:50 pm -
Nonstop0h 50m
Deal found 10/29![Southwest logo]()
$185
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 11/196:56 pm -
Nonstop1h 04m
Mon 11/238:48 am -
Nonstop1h 27m
Deal found 10/28![American Airlines logo]()
$186
This United Airlines deal was found by Cheapflights users on 10/25. 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 11/229:20 pm -
Nonstop0h 55m
Sun 11/296:47 am -
Nonstop1h 12m
Deal found 10/25![United Airlines logo]()
$268
This United Airlines deal was found by Cheapflights users on 10/25. 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 11/234:00 pm -
Nonstop1h 03m
Mon 11/308:35 am -
Nonstop1h 10m
Deal found 10/25![United Airlines logo]()
$246
This Southwest deal was found by Cheapflights users on 10/27. 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 11/244:20 pm -
1 stop6h 50m
Tue 12/14:05 pm -
1 stop5h 30m
Deal found 10/27![Southwest logo]()
$262
This United Airlines deal was found by Cheapflights users on 10/26. 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 11/257:30 am -
Nonstop1h 06m
Sat 11/289:20 am -
Nonstop1h 10m
Deal found 10/26![United Airlines logo]()
$227
This Southwest deal was found by Cheapflights users on 10/26. 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 11/2510:00 am -
Nonstop0h 50m
Sat 11/285:40 am -
Nonstop1h 05m
Deal found 10/26![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 10/29. 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.
Thu 11/265:40 am -
1 stop5h 15m
Thu 12/38:00 am -
1 stop7h 30m
Deal found 10/29![Southwest logo]()
$210
This United Airlines deal was found by Cheapflights users on 10/29. 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 11/279:20 pm -
Nonstop0h 55m
Fri 12/47:18 pm -
Nonstop1h 12m
Deal found 10/29![United Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 10/29. 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 11/279:15 pm -
Nonstop1h 00m
Fri 12/44:20 pm -
Nonstop0h 55m
Deal found 10/29![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 October 30, 2026.
Search for one-way flight options from Chicago to Milwaukee. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This American Airlines deal was found by Cheapflights users on 10/27. 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 11/245:59 pm -
Nonstop1h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![American Airlines logo]()
$93
This Southwest deal was found by Cheapflights users on 10/27. 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.
Thu 12/1010:10 am -
Nonstop0h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Southwest logo]()
$93
This American Airlines deal was found by Cheapflights users on 10/26. 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.
Thu 12/105:29 pm -
Nonstop1h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![American Airlines logo]()
$112
This Southwest deal was found by Cheapflights users on 10/28. 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 11/279:15 pm -
Nonstop1h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Southwest logo]()
$112
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/610:25 am -
Nonstop1h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![United Airlines logo]()
$132
This Southwest deal was found by Cheapflights users on 10/28. 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 12/610:10 am -
Nonstop0h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Southwest logo]()
$132
This United Airlines deal was found by Cheapflights users on 10/28. 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 11/281:55 pm -
Nonstop1h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![United Airlines logo]()
$135
This Southwest deal was found by Cheapflights users on 10/28. 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 11/2810:10 am -
Nonstop0h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Southwest logo]()
$135
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/228:48 am -
Nonstop1h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![United Airlines logo]()
$157
This United Airlines deal was found by Cheapflights users on 10/27. 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 11/159:20 pm -
Nonstop0h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![United Airlines logo]()
$164
This Southwest deal was found by Cheapflights users on 10/27. 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 11/1510:10 am -
Nonstop0h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Southwest logo]()
$164
This Southwest deal was found by Cheapflights users on 10/26. 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 3/1910:00 am -
Nonstop0h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Southwest logo]()
$165
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 October 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $185 (United Airlines) |
One-way from | $93 (American Airlines) |
Good one-way deal | $259 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 7,457,451 searches. Data last updated October 30, 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
Tue 11/24
5:59 pm-7:03 pm
Nonstop1h 04m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$93
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Tue 12/1
9:10 pm-10:15 pm
Nonstop1h 05m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$93
Quickest round-trip
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Thu 12/10
10:10 am-11:00 am
Nonstop0h 50m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$93
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Fri 11/27
9:15 pm-10:15 pm
Nonstop1h 00m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$112
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Sun 12/6
10:10 am-11:00 am
Nonstop0h 50m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$132
ChicagoMilwaukee
ORD Chicago O'Hare Intl - MKE Milwaukee-Mitchell
ORDMKE
Chicago O'Hare Intl
Sat 3/6
4:20 pm-5:13 pm
Nonstop0h 53m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$135
ChicagoMilwaukee
ORD Chicago O'Hare Intl - MKE Milwaukee-Mitchell
ORDMKE
Chicago O'Hare Intl
Sat 11/28
1:55 pm-2:58 pm
Nonstop1h 03m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$135
ChicagoMilwaukee
ORD Chicago O'Hare Intl - MKE Milwaukee-Mitchell
ORDMKE
Chicago O'Hare Intl
Tue 12/22
8:48 am-10:03 am
Nonstop1h 15m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$157
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Tue 11/10
9:10 pm-10:15 pm
Nonstop1h 05m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$164
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Fri 3/19
10:00 am-10:50 am
Nonstop0h 50m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$165
Showing 1-10 of 28 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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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 October 30, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 18% on flights from Chicago to Milwaukee by exploring options for tickets in the afternoon.
Reviews of airlines servicing Milwaukee
Get insights into the airlines that provide service to Milwaukee. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Milwaukee. Reviews last updated October 30, 2026.
Read through reviews of airlines operating flights from Chicago to Milwaukee, such as United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
7.7
Food
6.7
Comfort
7.3
Crew
8.1
Entertainment
7.1
Overall
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Boarding
7.7
Food
6.7
Comfort
7.3
Crew
8.1
Entertainment
7.1
Overall
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
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 locationsPort Washington
Sheboygan
New Berlin
Oak Creek
Wauwatosa
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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
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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 7,457,451 searches. Data last updated October 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$179 | Average$224 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$181 | Average$320 | FlexibilityNo cancel fee | On-time69% |