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Book cheap flights from Wisconsin to Chicago (round-trip)

Airports
Origin
Milwaukee
$227
only
$227
Green Bay
$173
only
$173
Madison
$173
only
$173
La Crosse
$173
only
$173
Appleton
$173
only
$173
Destination
Chicago
$173
only
$173
$210
only
$210
Tue, Apr 3
GRB
ORD
1h 10m
Tue, Apr 10
ORD
GRB
1h 01m
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 13 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
GRB
ORD
Excellent 8.3

Crew was great and quiet flight

No wifi or video system on plane

EWR
BTV
Okay 4.6

When boarding, the agent said we had to check our rollaboards because they were our of overhead bin space. Hen we entered the plane, we saw that the entire back half of the plane had empty bins, but by that time it was too last to retrieve our bags.

GRB
ORD
Mediocre 2.0

Nothing

Lufthansa canceled the flights and blamed united airlines. The united airlines would not help and finally ended up having to stay in Frankfurt and now have to leave for Lisbon tomorrow and then onwards.

SLC
SFO
Good 6.3

The crew were very nice and polite.

No snack options. Only pretzels. Seat cushion very thin.

SFO
CDG
Excellent 8.6

You’re entertainment options far exceed your competitors. The food (vegetarian) was excellent.

Wed, Apr 18
LSE
ORD
1h 11m
Sun, Apr 22
ORD
LSE
1h 07m
Trip: 5 days
6.6GoodShow reviews
Overall 6.6 Good
Based on 1 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
YYZ
LAX
Okay 5.6

Crew was great!

Was really poor choice of food.

DFW
IAH
Okay 4.0

Crew

Delayed, old aircraft, no food, no entertainment

LSE
ORD
Good 6.6

Was appropriately warned that British Airways was having computer problems

JFK
MAD
Good 6.6

The food was good and the crew was nice.

We were delayed for 90 minutes. And the entertainment options were awful for such a long flight.

DFW
SFO
Mediocre 3.3

The only positive thing to be said for the flight was that the seat was not uncomfortable.

Entertainment system did not work during entire flight; crew (stewards) lied to passengers on the ground that it would work after takeoff, only admitting after we were in the air that they had been told by the technicians it would not work at all. Crew did not respond to call lights when pressed (in First Class), nor did they know how to operate the power system.

Thu, Apr 19
GRB
MDW
5h 12m
Sun, Apr 22
MDW
GRB
3h 40m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16068 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
DTW
AMS
Good 7.0

The vegan meal was not good

AMS
JFK
Okay 5.6

Food was better than the usual airline food. We also got a Valentine's day chocolate.

seats too narrow, barely have room to sit and stand. No USB charger

AMS
PDX
Mediocre 3.0

NOTHING

GPT
ATL
Good 6.0

The crew was organized and made us all laugh, and had a great personality.

I upgraded my seat and paid extra for one with more room. And I wasn’t impressed with my upgrade, doesn’t feel like more leg than regular seats. Comfort was below average.

ATL
EYW
Excellent 8.6

Once we hit the coast we skirted down the coas of Florida which provided a spectacular view. The approach and landing at Key West airport was thrilling and absolutely perfect. We’ve flown Delta many times but this was our first but not last time to Key West.

Nothing

Tue, Apr 3
MKE
ORD
0h 58m
Mon, Apr 9
ORD
MKE
0h 50m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Apr 3
ATW
ORD
1h 08m
Tue, Apr 10
ORD
ATW
0h 57m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 12 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
ATW
ORD
Excellent 8.0

Crew was nice and boarding went smooth

seats were very close together

ATW
ORD
Okay 5.0

Why the hell would you sell a flight with a 40 minute transfer between a domestic and international flight that were in different terminals?! The only reason I made it was because the airport crew was great in helping me get through the airport quickly. And the only reason my luggage made it on time was because my flight was delayed for two hours.

LAX
IAH
Excellent 8.0

On time departure and arrive

No much variety of movies and tv shows to watch

SLC
SFO
Good 6.3

The crew were very nice and polite.

No snack options. Only pretzels. Seat cushion very thin.

SEA
IAH
Okay 4.3

The final leg on a Delta flight was very pleasant.

My final destination had a total of two flights a day available on United. The first leg I originally booked was pushed back and back and back b/c of weather. I was stuck at the Houston airport for 12 hrs after agreeing to take another one-stop flight, making it a total of three flights taking more than 24 hrs. I then had to cry to even get food vouchers. Where would I sleep? On the flor in the Houston airport, the most inhospitable airport I’ve ever been in. They have a hotel *in* the airport, but because it was “weather” causing the delay they refused to put me up. There was a woman whose birthday it was and she was trying to get to her husband having surgery the next day and a double amputee all in the same boat. It was absolutely a nightmare. I got maybe 1 hour sleep the whole night despite trying for 5-6. Never again will I fly United unless under duress or some emergency.

Sat, May 12
MSN
ORD
0h 58m
Sun, May 13
ORD
MSN
0h 56m
Trip: 2 days
9.5ExcellentShow reviews
Overall 9.5 Excellent
Based on 4 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
DFW
IAH
Okay 4.0

Crew

Delayed, old aircraft, no food, no entertainment

MSN
ORD
Excellent 10.0

Everything was just fine. I liked having my own seat in my own row.

Nothing.

DFW
COS
Good 7.0

Everyone was nice

No gluten free snacks. Flight was late

PDX
PHX
Excellent 10.0

A nice uneventful trip

JFK
CDG
Excellent 10.0

The food

There’s no WiFi

Fri, Apr 20
GRB
ORD
1h 08m
Sun, Apr 22
ORD
GRB
1h 07m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 13 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
EWR
BTV
Okay 4.6

When boarding, the agent said we had to check our rollaboards because they were our of overhead bin space. Hen we entered the plane, we saw that the entire back half of the plane had empty bins, but by that time it was too last to retrieve our bags.

LAX
IAH
Excellent 8.0

On time departure and arrive

No much variety of movies and tv shows to watch

SLC
SFO
Good 6.3

The crew were very nice and polite.

No snack options. Only pretzels. Seat cushion very thin.

GRB
ORD
Excellent 10.0

This flight was On Time..

GRB
ORD
Excellent 8.0

Notices of changes before anyone else got them like gate changes.

Running through Ohare to catch my connection

Tue, May 15
LSE
ORD
1h 18m
Sat, May 19
ORD
LSE
1h 08m
Trip: 5 days
6.6GoodShow reviews
Overall 6.6 Good
Based on 1 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
PHL
BWI
Okay 4.6

Got two seats to myself.

I don't even know who our flight attendants were. Did we have them? Isn't that a requirement?? Guy in seat in front of me was super rude (yes, I know it's not the airline's fault.). Terrible turbulence (again, not AA's fault).

MIA
ATL
Excellent 8.0

Cookies they offered were vegan friendly.

Had to sit in the very last row which didn’t recline.

HSV
CLT
Excellent 8.3

Too cramped.

MUC
PHL
Okay 4.6

2 hour late departure. could not get there story strait on why the delay, finally they went with weather delay. steward reminded me of a bunch of people unhappy with there jobs. need to work on customer service

DFW
SFO
Mediocre 3.3

The only positive thing to be said for the flight was that the seat was not uncomfortable.

Entertainment system did not work during entire flight; crew (stewards) lied to passengers on the ground that it would work after takeoff, only admitting after we were in the air that they had been told by the technicians it would not work at all. Crew did not respond to call lights when pressed (in First Class), nor did they know how to operate the power system.

Fri, Apr 20
ATW
ORD
1h 07m
Sun, Apr 22
ORD
ATW
1h 05m
Trip: 3 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 12 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
LAX
IAH
Excellent 8.0

On time departure and arrive

No much variety of movies and tv shows to watch

ATW
ORD
Okay 5.0

Why the hell would you sell a flight with a 40 minute transfer between a domestic and international flight that were in different terminals?! The only reason I made it was because the airport crew was great in helping me get through the airport quickly. And the only reason my luggage made it on time was because my flight was delayed for two hours.

DUB
EWR
Good 7.6

Great selection of movies; on time departure and arrival much appreciated.

Food was poor

LHR
IAH
Good 7.6

The movies, the crew, the flight itself.

The food was horrible. Also, all of my ticket information said Brussels Airlines but there's no such thing. It made it very confusing because on my departure I was looking for Brussels, but it was actually United I needed to look for.

GEG
SFO
Excellent 9.0

Need addl gate capacity at sfo including non-jetway options when other better options are unavailable.

Thu, May 31
GRB
ORD
1h 14m
Sun, Jun 10
ORD
GRB
0h 59m
Trip: 11 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 2 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
YYZ
LAX
Okay 5.6

Crew was great!

Was really poor choice of food.

PDX
PHX
Excellent 10.0

A nice uneventful trip

MUC
PHL
Okay 4.6

2 hour late departure. could not get there story strait on why the delay, finally they went with weather delay. steward reminded me of a bunch of people unhappy with there jobs. need to work on customer service

JFK
CDG
Excellent 10.0

The food

There’s no WiFi

DFW
IAH
Okay 4.0

Crew

Delayed, old aircraft, no food, no entertainment

Tue, May 29
ATW
ORD
1h 08m
Sun, Jun 10
ORD
ATW
1h 06m
Trip: 13 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 12 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
CDG
IAD
Excellent 9.0

The entertainment interface and selection was fantastic!

Minor, but an arm rest would not stay up. Also, let's face it, the food food is never excellent, rarely good, but understandably hard to make so.

ATW
ORD
Okay 5.0

Why the hell would you sell a flight with a 40 minute transfer between a domestic and international flight that were in different terminals?! The only reason I made it was because the airport crew was great in helping me get through the airport quickly. And the only reason my luggage made it on time was because my flight was delayed for two hours.

ATW
ORD
Excellent 8.0

Crew was nice and boarding went smooth

seats were very close together

LAX
IAH
Excellent 8.0

On time departure and arrive

No much variety of movies and tv shows to watch

DUB
EWR
Good 7.6

Great selection of movies; on time departure and arrival much appreciated.

Food was poor

Tue, Jun 12
GRB
ORD
1h 15m
Tue, Jun 26
ORD
GRB
0h 59m
Trip: 15 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 2 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
FRA
DFW
Excellent 10.0

Plenty of entertainment.

It’s just a long flight there’s no way to change that.

DFW
SEA
Excellent 10.0

The fight was not over crowded.

DFW
SFO
Mediocre 3.3

The only positive thing to be said for the flight was that the seat was not uncomfortable.

Entertainment system did not work during entire flight; crew (stewards) lied to passengers on the ground that it would work after takeoff, only admitting after we were in the air that they had been told by the technicians it would not work at all. Crew did not respond to call lights when pressed (in First Class), nor did they know how to operate the power system.

GRB
ORD
Excellent 8.0

Only 30 minutes or so to ORD from GRB Paid with AA points at 7,500 miles each way for a weekend in Chicago

JFK
CDG
Excellent 10.0

The food

There’s no WiFi

Fri, Jul 27
LSE
MDW
6h 22m
Mon, Jul 30
MDW
LSE
6h 23m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16068 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
LGA
MCI
Excellent 10.0

The service and non stop smooth ride. Boarding was a new experiance taking a bus to the plane. Was quick and crew helpful storing my carryon. Everyone very helpful.

MCI
LGA
Good 6.0

Too crowded overhead storage got filled right away. Had to place my bag under seat. Could not extend my legs.

ATL
EYW
Excellent 8.6

Once we hit the coast we skirted down the coas of Florida which provided a spectacular view. The approach and landing at Key West airport was thrilling and absolutely perfect. We’ve flown Delta many times but this was our first but not last time to Key West.

Nothing

OKC
DTW
Excellent 10.0

As usual

Landing was a bit rough

CUN
MSP
Excellent 10.0

The flights were on time and they did two drink and snack services. Great crew!

Thu, May 31
MSN
ORD
0h 58m
Sun, Jun 10
ORD
MSN
0h 48m
Trip: 11 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 39 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
MSN
ORD
Excellent 8.0

They kept us well hydrated

How far I had to get to me next flight in Chicago

MSN
ORD
Excellent 8.0

Getting a seat in economy plus! (But I think that happened because I had trouble using the online seat booking process and couldn't get a seat assignment till I got to the gate for my Albany flight, probably the only seat available) also liked arriving early in Albany.

Arriving at the end of terminal C and having to trek to the end of terminal B for my connecting flight. Supposedly a one hour window, but by the time I got off, and made that enormous trek, no time to get a meal. Going to Madison flights left from almost adjoining gates. Lovely!

MSN
ORD
Okay 4.6

Gate agent handled impossible situation well

flight was canceled due to mechanical problems on two of the airplanes

MSN
ORD
Okay 5.3

The actual crew on the flight was lovely and apologetic, did everything they could to help us despite the delays. At least that's something.

Delayed for over an hour but not notified of the length of the delay in a fashion which would allow me to drive the 2 hours to Chicago in order to make my connection. Repeatedly told the connecting flight was the last one out of the entire airport to my final destination. Heard other travelers discussing that they had been rebooked onto an alternate airline and then found a later flight on Kayak, walked up to podium and asked to be rebooked on that specific flight, which they grudgingly did. Of note, I was repeatedly reassured that they were "sure" I would make my connection without a problem and to stop worrying so much. My flight left out of Madison 2 minutes after my connection departed Chicago. I usually fly a different airline, whose flights out of Madison were all on time that day, and will do so in the future despite more expensive ticket. The actual crew on the flight was lovely and apologetic, did everything they could to help us despite the delays. At least that's something.

MSN
ORD
Mediocre 2.0

There is nothing positive to say.

Plane was delayed by 8 hours. We boarded and unboarded the plane 3 times. Why didn't they just cancel the flight? I missed my connecting flight. No food or beverage service. Didn't even let us use the airplane bathroom after a long delay. I paid to check my luggage and they LOST it and sent it to the wrong airport.

Tue, Jul 24
LSE
ORD
1h 09m
Tue, Aug 7
ORD
LSE
1h 07m
Trip: 15 days
6.6GoodShow reviews
Overall 6.6 Good
Based on 1 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
JFK
MAD
Good 6.6

The food was good and the crew was nice.

We were delayed for 90 minutes. And the entertainment options were awful for such a long flight.

HSV
CLT
Excellent 8.3

Too cramped.

LSE
ORD
Good 6.6

Was appropriately warned that British Airways was having computer problems

DCA
ORF
Mediocre 2.0

Long time sitting in the plane without any updates from the crew. Very inefficient process in re-booking passengers and switching planes. Maintenance issues are are a trend at American Airlines.

IND
PHL
Good 6.3

I got to sneak into the economy plus seats and no one said anything.

Flight attendants clearly did not like each other and argued constantly. Sub-par coffee (even by international standards).

Tue, Mar 6
MKE
ORD
0h 56m
Thu, Mar 8
ORD
MKE
0h 49m
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Jun 2
ATW
ORD
1h 08m
Sun, Jun 10
ORD
ATW
1h 06m
Trip: 9 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 12 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
ATW
ORD
Excellent 10.0

The flight was a lot more than what I had expected. I have spent my life staying in many hotel rooms and my fair share in planes, this was an excellent flight. It was on time both from Appleton to Chicago and Chicago to Houston. I have no complaints.

SLC
SFO
Good 6.3

The crew were very nice and polite.

No snack options. Only pretzels. Seat cushion very thin.

ATW
ORD
Excellent 8.0

Crew was nice and boarding went smooth

seats were very close together

ATW
ORD
Okay 5.0

Why the hell would you sell a flight with a 40 minute transfer between a domestic and international flight that were in different terminals?! The only reason I made it was because the airport crew was great in helping me get through the airport quickly. And the only reason my luggage made it on time was because my flight was delayed for two hours.

LHR
IAH
Good 7.6

The movies, the crew, the flight itself.

The food was horrible. Also, all of my ticket information said Brussels Airlines but there's no such thing. It made it very confusing because on my departure I was looking for Brussels, but it was actually United I needed to look for.

Fri, Aug 17
MSN
ORD
0h 58m
Sun, Aug 19
ORD
MSN
1h 00m
Trip: 3 days
9.5ExcellentShow reviews
Overall 9.5 Excellent
Based on 4 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
STL
DFW
Good 7.3

Smooth boarding. On time flight

No gluten free snacks:(

MUC
PHL
Okay 4.6

2 hour late departure. could not get there story strait on why the delay, finally they went with weather delay. steward reminded me of a bunch of people unhappy with there jobs. need to work on customer service

MSN
ORD
Excellent 10.0

Everything was just fine. I liked having my own seat in my own row.

Nothing.

YYZ
LAX
Okay 5.6

Crew was great!

Was really poor choice of food.

JFK
CDG
Excellent 10.0

The food

There’s no WiFi

Tue, Jun 26
MSN
ORD
0h 58m
Tue, Jul 3
ORD
MSN
1h 02m
Trip: 8 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 39 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
MSN
ORD
Okay 4.6

Gate agent handled impossible situation well

flight was canceled due to mechanical problems on two of the airplanes

MSN
ORD
Excellent 8.0

Getting a seat in economy plus! (But I think that happened because I had trouble using the online seat booking process and couldn't get a seat assignment till I got to the gate for my Albany flight, probably the only seat available) also liked arriving early in Albany.

Arriving at the end of terminal C and having to trek to the end of terminal B for my connecting flight. Supposedly a one hour window, but by the time I got off, and made that enormous trek, no time to get a meal. Going to Madison flights left from almost adjoining gates. Lovely!

MSN
ORD
Okay 5.3

The actual crew on the flight was lovely and apologetic, did everything they could to help us despite the delays. At least that's something.

Delayed for over an hour but not notified of the length of the delay in a fashion which would allow me to drive the 2 hours to Chicago in order to make my connection. Repeatedly told the connecting flight was the last one out of the entire airport to my final destination. Heard other travelers discussing that they had been rebooked onto an alternate airline and then found a later flight on Kayak, walked up to podium and asked to be rebooked on that specific flight, which they grudgingly did. Of note, I was repeatedly reassured that they were "sure" I would make my connection without a problem and to stop worrying so much. My flight left out of Madison 2 minutes after my connection departed Chicago. I usually fly a different airline, whose flights out of Madison were all on time that day, and will do so in the future despite more expensive ticket. The actual crew on the flight was lovely and apologetic, did everything they could to help us despite the delays. At least that's something.

MSN
ORD
Okay 4.0

Delays and poor communication. Ended up on other airline and 14 hrs to get from Madison, WI to Baltimore, MD

MSN
ORD
Excellent 8.0

They kept us well hydrated

How far I had to get to me next flight in Chicago

Mon, Apr 2
MSN
ORD
1h 01m
Mon, Apr 23
ORD
MSN
0h 53m
Trip: 22 days
9.5ExcellentShow reviews
Overall 9.5 Excellent
Based on 4 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
YYZ
LAX
Okay 5.6

Crew was great!

Was really poor choice of food.

DFW
SFO
Mediocre 3.3

The only positive thing to be said for the flight was that the seat was not uncomfortable.

Entertainment system did not work during entire flight; crew (stewards) lied to passengers on the ground that it would work after takeoff, only admitting after we were in the air that they had been told by the technicians it would not work at all. Crew did not respond to call lights when pressed (in First Class), nor did they know how to operate the power system.

DFW
SEA
Excellent 10.0

The fight was not over crowded.

STL
DFW
Good 7.3

Smooth boarding. On time flight

No gluten free snacks:(

PDX
PHX
Excellent 10.0

A nice uneventful trip

Wisconsin to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from Wisconsin
Flight Price $173
Airlines United, American Airlines, Delta
*
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