Cheap Flights from Milwaukee, WI to Chicago, IL from $130
On Cheapflightsplus.com you will find 11 direct and 152 connecting flights from Milwaukee to Chicago. You can compare airfare deals from 5 airlines and multiple travel sites from $130, book and save on cheap plane tickets and last minute offers. Also check out MKE-CHI flight schedule to find best flight time, convenient departure and arrival airports.
Find One-Way and Round-Trip Milwaukee to Chicago Flight Deals
To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights».
To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight.
Cheapest flights in November: $130 (one-way), $223 (round-trip).
Direct flights
Check prices for return flight
Best Flights from Milwaukee to Chicago Today
Take a look at the list of non stop flights and flights with layovers from Milwaukee to Chicago with the lowest price of $130. The fastest direct flight takes 1h 4m and the fastest connecting – 6h 1m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $237 | 08:35 Milwaukee General Mitchell | 09:39 Chicago O'Hare International | 1h 4m | United Airlines | UA5402 |
| from $130 | 18:30 Milwaukee General Mitchell | 15:45+1 день Chicago O'Hare International | 21h 15m layover 18h 17m - Minneapolis | Sun Country Airlines | SY1816 SY259 |
| from $172 | 17:16 Milwaukee General Mitchell | 05:25+1 день Chicago O'Hare International | 12h 9m layover 3h 42m - Los Angeles | Spirit Airlines | NK1867 NK1103 |
| from $189 | 20:51 Milwaukee General Mitchell | 18:43+1 день Chicago O'Hare International | 21h 52m layover 15h 52m - Orlando | Spirit Airlines | NK2910 NK506 |
| from $189 | 20:51 Milwaukee General Mitchell | 19:58+1 день Chicago O'Hare International | 23h 7m layover 17h 5m - Orlando | Spirit Airlines | NK2910 NK1109 |
| from $223 | 16:37 Milwaukee General Mitchell | 15:31+1 день Chicago O'Hare International | 22h 54m layover 17h 2m - Orlando | Spirit Airlines | NK1351 NK1369 |
| from $224 | 06:30 Milwaukee General Mitchell | 23:59 Chicago O'Hare International | 17h 29m layover 9h 5m - Seattle | Hawaiian Airlines | HA6250 HA6819 |
| from $225 | 06:30 Milwaukee General Mitchell | 16:49 Chicago O'Hare International | 10h 19m layover 1h 50m - Seattle | Alaska Airlines | AS242 AS429 |
| from $158 | 14:51 Milwaukee General Mitchell | 16:46+1 день Chicago O'Hare International | 25h 55m layover 2h 2m - Las Vegas 14h 20m - Los Angeles | Spirit Airlines | NK1445 NK1551 NK1105 |
| from $171 | 09:22 Milwaukee General Mitchell | 20:00+1 день Chicago O'Hare International | 34h 38m layover 6h 44m - Detroit 22h 40m - New York | Spirit Airlines | NK1254 NK1078 NK1179 |
| from $172 | 09:22 Milwaukee General Mitchell | 20:00+1 день Chicago O'Hare International | 34h 38m layover 5h 54m - Detroit 23h 30m - New York | Spirit Airlines | NK1254 NK1085 NK1179 |
| from $198 | 07:45 Milwaukee General Mitchell | 09:55+1 день Chicago O'Hare International | 26h 10m layover 10h 33m - Detroit 8h 11m - Miami | Spirit Airlines | NK3901 NK3930 NK2 |
| from $206 | 20:51 Milwaukee General Mitchell | 22:28+1 день Chicago O'Hare International | 25h 37m layover 6h 19m - Orlando 12h 42m - Atlanta | Spirit Airlines | NK2910 NK1850 NK1200 |
| from $213 | 20:51 Milwaukee General Mitchell | 22:28+1 день Chicago O'Hare International | 25h 37m layover 9h 26m - Orlando 9h 36m - Atlanta | Spirit Airlines | NK2910 NK3377 NK1200 |
| from $214 | 09:22 Milwaukee General Mitchell | 20:00 Chicago O'Hare International | 10h 38m layover 2h 30m - Detroit 2h 55m - New York | Spirit Airlines | NK1254 NK1893 NK1179 |
| from $226 | 20:51 Milwaukee General Mitchell | 09:55+1 день Chicago O'Hare International | 13h 4m layover 4h 49m - Orlando 1h 5m - Miami | Spirit Airlines | NK2910 NK195 NK2 |
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on July 12, 2025
Flight Schedule Milwaukee (Wisconsin) to Chicago (Illinois)
Full flight schedule will help you in detecting at what time planes fly from Milwaukee to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
| Departure | Arrival | Flight Details | Flight Duration | Price |
|---|---|---|---|---|
|
05:15 — 06:20
|
05:15 — 06:20
UA5799
United Airlines
Milwaukee — Chicago
|
1h 5m |
Find flight
from$237 |
|
|
06:00 — 07:10
|
06:00 — 07:10
UA5996
United Airlines
Milwaukee — Chicago
|
1h 10m |
Find flight
from$237 |
|
|
07:00 — 08:05
|
07:00 — 08:05
UA4803
United Airlines
Milwaukee — Chicago
|
1h 5m |
Find flight
from$237 |
|
|
08:35 — 09:39
|
08:35 — 09:39
UA5402
United Airlines
Milwaukee — Chicago
|
1h 4m |
Find flight
from$237 |
|
|
10:45 — 11:50
|
10:45 — 11:50
UA4716
United Airlines
Milwaukee — Chicago
|
1h 5m |
Find flight
from$237 |
|
|
10:50 — 12:00
|
10:50 — 12:00
UA5347
United Airlines
Milwaukee — Chicago
|
1h 10m |
Find flight
from$237 |
|
|
10:50 — 12:00
|
10:50 — 12:00
UA4691
United Airlines
Milwaukee — Chicago
|
1h 10m |
Find flight
from$238 |
|
|
12:10 — 13:15
|
12:10 — 13:15
UA4740
United Airlines
Milwaukee — Chicago
|
1h 5m |
Find flight
from$237 |
|
|
15:45 — 16:50
|
15:45 — 16:50
UA5502
United Airlines
Milwaukee — Chicago
|
1h 5m |
Find flight
from$237 |
|
|
17:31 — 18:36
|
17:31 — 18:36
UA5648
United Airlines
Milwaukee — Chicago
|
1h 5m |
Find flight
from$237 |
|
|
17:31 — 18:36
|
17:31 — 18:36
UA3700
United Airlines
Milwaukee — Chicago
|
1h 5m |
Find flight
from$238 |
|
|
06:30 — 23:59
|
06:30 — 08:50
HA6250
Hawaiian Airlines
Milwaukee — Seattle
9h 5m stop
17:55 — 23:59
HA6819
Hawaiian Airlines
Seattle — Chicago
|
17h 29m including layover |
Find flight
from$224 |
|
|
06:30 — 16:49
|
06:30 — 08:53
AS242
Alaska Airlines
Milwaukee — Seattle
1h 50m stop
10:50 — 16:57
AS429
Alaska Airlines
Seattle — Chicago
|
10h 19m including layover |
Find flight
from$225 |
|
|
16:37 — 15:31
+1 day
|
16:37 — 20:21
NK1351
Spirit Airlines
Milwaukee — Orlando
17h 2m stop
13:23 — 15:31
NK1369
Spirit Airlines
Orlando — Chicago
|
22h 54m including layover |
Find flight
from$223 |
|
|
17:16 — 05:25
+1 day
|
17:16 — 19:38
NK1867
Spirit Airlines
Milwaukee — Los Angeles
3h 42m stop
23:20 — 05:25
NK1103
Spirit Airlines
Los Angeles — Chicago
|
12h 9m including layover |
Find flight
from$172 |
|
|
17:16 — 16:46
+1 day
|
17:16 — 19:38
NK1867
Spirit Airlines
Milwaukee — Los Angeles
14h 58m stop
10:36 — 16:46
NK1105
Spirit Airlines
Los Angeles — Chicago
|
23h 30m including layover |
Find flight
from$172 |
|
|
18:30 — 15:45
+1 day
|
18:30 — 19:49
SY1816
Sun Country Airlines
Milwaukee — Minneapolis
18h 17m stop
15:36 — 17:15
SY259
Sun Country Airlines
Minneapolis — Chicago
|
21h 15m including layover |
Find flight
from$130 |
|
|
20:51 — 18:43
+1 day
|
20:51 — 00:41
NK2910
Spirit Airlines
Milwaukee — Orlando
15h 52m stop
16:33 — 18:43
NK506
Spirit Airlines
Orlando — Chicago
|
21h 52m including layover |
Find flight
from$189 |
|
|
20:51 — 19:58
+1 day
|
20:51 — 00:41
NK2910
Spirit Airlines
Milwaukee — Orlando
17h 5m stop
17:46 — 19:58
NK1109
Spirit Airlines
Orlando — Chicago
|
23h 7m including layover |
Find flight
from$189 |
|
|
07:45 — 14:16
+1 day
|
07:45 — 09:55
NK3901
Spirit Airlines
Milwaukee — Detroit
5h 54m stop
15:49 — 18:53
NK291
Spirit Airlines
Detroit — Miami
17h stop
11:53 — 14:16
NK3201
Spirit Airlines
Miami — Chicago
|
30h 31m including layover |
Find flight
from$180 |
|
|
07:45 — 09:55
+1 day
|
07:45 — 09:55
NK3901
Spirit Airlines
Milwaukee — Detroit
10h 33m stop
20:28 — 23:29
NK3930
Spirit Airlines
Detroit — Miami
8h 11m stop
07:40 — 09:55
NK2
Spirit Airlines
Miami — Chicago
|
26h 10m including layover |
Find flight
from$198 |
|
|
09:22 — 20:00
+1 day
|
09:22 — 11:25
NK1254
Spirit Airlines
Milwaukee — Detroit
6h 44m stop
18:09 — 19:50
NK1078
Spirit Airlines
Detroit — New York
22h 40m stop
18:30 — 20:00
NK1179
Spirit Airlines
New York — Chicago
|
34h 38m including layover |
Find flight
from$171 |
|
|
09:22 — 20:00
+1 day
|
09:22 — 11:25
NK1254
Spirit Airlines
Milwaukee — Detroit
5h 54m stop
17:19 — 19:00
NK1085
Spirit Airlines
Detroit — New York
23h 30m stop
18:30 — 20:00
NK1179
Spirit Airlines
New York — Chicago
|
34h 38m including layover |
Find flight
from$172 |
|
|
14:51 — 16:46
+1 day
|
14:51 — 16:57
NK1445
Spirit Airlines
Milwaukee — Las Vegas
2h 2m stop
18:59 — 20:16
NK1551
Spirit Airlines
Las Vegas — Los Angeles
14h 20m stop
10:36 — 16:46
NK1105
Spirit Airlines
Los Angeles — Chicago
|
25h 55m including layover |
Find flight
from$158 |
|
|
14:51 — 16:46
+1 day
|
14:51 — 16:57
NK1445
Spirit Airlines
Milwaukee — Las Vegas
4h 40m stop
21:37 — 22:50
NK1657
Spirit Airlines
Las Vegas — Los Angeles
11h 46m stop
10:36 — 16:46
NK1105
Spirit Airlines
Los Angeles — Chicago
|
25h 55m including layover |
Find flight
from$158 |
|
|
16:37 — 14:04
+1 day
|
16:37 — 20:21
NK1351
Spirit Airlines
Milwaukee — Orlando
12h 6m stop
08:27 — 10:11
G43064
Allegiant Air
Orlando — Knoxville
3h 20m stop
13:31 — 14:04
G43027
Allegiant Air
Knoxville — Chicago
|
21h 27m including layover |
Find flight
from$221 |
|
|
18:30 — 16:46
+1 day
|
18:30 — 19:49
SY1816
Sun Country Airlines
Milwaukee — Minneapolis
1h 5m stop
20:54 — 22:41
SY429
Sun Country Airlines
Minneapolis — Los Angeles
11h 55m stop
10:36 — 16:46
NK1105
Spirit Airlines
Los Angeles — Chicago
|
22h 16m including layover |
Find flight
from$224 |
|
*Departure and arrival times - local. Updated on July 12, 2025
Flight Information
Below we will explain in detail what the flights cost on the destination from Milwaukee to Chicago depends on and how to choose the most interesting flight option for you.
Distance between Milwaukee and Chicago is 120 miles. Time difference between the cities is 0h. Airplanes depart 05:15 to 20:51 from 3 Milwaukee airports and arrive 05:15 to 20:51 to 7 Chicago airports. Average flight time is 1h 5m.
- The fastest flight 1h 4m
- Average flight time 1h 5m
- The earliest flight 05:15
- The latest flight 20:51
- Distance 75 ml
The cheapest months to travel to Chicago are july (from 130 $), august (from 180 $), december (from 191 $).
The most expensive months are november (from 286 $), may (from 238 $), june (from 237 $).
What is the lowest airfare Milwaukee to Chicago?
The cheapest plane ticket found by our users is $130. This airfare is for economy class on one-way SY1816 flight by Sun Country Airlines for July 24, 2025 which leaves General Mitchell in Milwaukee at 18:30 am and arrives at Chicago O'Hare International at 15:45.
Economy class
$130
Business class
?
First class
?
Popular Airlines on the Route
The flight Milwaukee — Chicago is served by 5 regular airlines and 2 low-cost airlines. Most of the flights on this route are operated by Alaska Airlines - 9 departures per week at the price of from $ 225 . And the most expensive tickets are offered by United Airlines airline - from $ 722.
Direct flights
There are 11 nonstop flights on the route. The fastest direct flight is UA5402 by United Airlines takes 1h 4m and the cheapest is SY1816 by Sun Country Airlines for $237.
- UA - United Airlinesfrom $237Find
See more direct flights
Connecting Flights
There are 152 flights with layovers on the route. The fastest connecting flight is UA1401 by United Airlines takes 6h 1m and the cheapest is SY1816 by Sun Country Airlines for $130.
- AS - Alaska Airlinesfrom $225Find
- SY - Sun Country Airlinesfrom $130Find
- HA - Hawaiian Airlinesfrom $224Find
- UA - United Airlinesfrom $277Find
- NK - Spirit Airlinesfrom $158Find
See more connecting flights
Airports
You can fly from Milwaukee to Chicago from 3 airports (Lawrence J Timmerman, Milwaukee General Mitchell, General Mitchell).
Milwaukee airports
- Lawrence J Timmerman-MWCFind
- Milwaukee General Mitchell-ZMLFind
- General Mitchell-MKEfrom $130Find
Chicago airports
- O'Hare International-ORDFind
- Midway-MDWFind
- Dupage County-DPAFind
- Chicago FSS-CHIFind
- Merrill C Meigs (closed)-CGXFind
- Pal-Waukee-PWKFind
- Chicago NAS-NOHFind
Airplanes
There are flights to Chicago from Milwaukee by 5 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.
Top Domestic Destinations from Milwaukee
You may also consider searching for discounted plane tickets to some other popular places from Milwaukee within United States.
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Top International Destinations from Milwaukee
Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.
- from $57Find
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How to book a plane ticket yourself?
- Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
- Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
- Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
- Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
- That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.
To find a plane ticket, please select dates.