Overall Summary

Traveling by Amtrak can be a good option when traveling to Milwaukee from within the Midwest. This is more true in some cases than others.

Amtrak is a great option for those coming from:

Chicago, IL
Minneapolis, MN
La Crosse, WI

Amtrak is an ok option for those coming from:

Detroit, MI
Grand Rapids, MI

Amtrak is a reasonable senic option for part of the trip for those coming from:

Cleveland, OH: Only on the return, and only in first class.

Amtrak is a poor option for those coming from:

Saint Louis, MO
Indianapolis, IN

Broader Information

For broader information, please see the following links:

Midwest City Specifics

An aggregated summary of the specifics for various key cities in the Midwest is provided below. The times and prices shown here are based on the assumption someone is traveling to the LeSS UnConference on June 27-28, and also planning to attend the Certified LeSS Practitioner course which preceeds it on June 24-26.

Chicago, IL

Notes

The Hiawatha runs between Chicago and Milwaukee every couple hours during the day. The trip takes around 1h30m in each direction. A flexible coach ticket is around $43 in each way during peak times, and a good bit less in off-peak times.

There isn’t an easier way to go back and forth between dowtown Chicago and downtown Milwaukee. For people in the northern suburbs of Chicago, driving will be a better option.

You can find a table of all the travel times in both directions on Amtrak’s dedicated Hiawatha page.

The northbound Borealis 1333 and the Hiawatha 333 are the same train. Similarly, the Borealis 1340 and the Hiawatha 340 are the same train.

Be warned, the last northbound Hiawatha 8307 “train” of the day at 9:15 p.m. is really a bus. It is not a pleasurable experience when compared to the train. This is shown on the table, just remember to pay attention to the fact.

Almost every Amtrak route to Milwaukee involves traveling on the Hiawatha for the final segment. The only exception is the Empire Builder/Borealis route. The Empire Builder/Borealis route is how people from Minneapolis and La Crosse get to Milwaukee. The Empire Builder route starts off in Seattle and Portland and runs roughly parallel to the Canadian border.

Summary

The Hiawatha is super easy, costs less than gas and parking, and avoids driving in heavy Chicago traffic. If you live near downtown Chicago, the Hiawatha is your best bet. Otherwise, you should probably just drive.

Minneapolis, MN

Outbound

*MSP;8:50am->2:57pm;MKE Empire Builder (coach:$66/first:$231) 6h7m
!*MSP;11:50pm->5:40pm;MKE Borealis (coach:$82/business:$158) 5h50m

Return

!*MKE;12:39pm->6;29pm;MSP Borealis(coach:$54/business:$119) 5h50m
*MKE;4:45pm->10:56pm;MSP Empire Builder (coach:$66/first:$385) 6h11m

Notes

The Borealis will be timely in both directions since it is a regional route which travels back and forth between MSP and CHI. There is no checked luggage currently on the Borealis, yet the carry-on allowance is very generous compared to flying.

The Empire Builder is likely to be delayed going to Milwaukee since it originates on the west coast. On the return, the Empire Builder should be timely since it originates nearby in Chicago.

Delta has lots of non-stop flights between MSP and MKE. The flights last around 1h20m. A flight in coach cost around $474 round-trip.

Driving between Minneapolis and Milwaukee takes just over 5 hours, not counting any stops for gas or food.

Exclamation indicated route pricing example:

Outbound: coach: $82, business: $158
Return: coach: $54, business: $119

Summary

There isn’t a bad choice here. Amtrak, driving, and flying all work fairly well. Amtrak and driving are the most cost effective choices. Flying is only a little faster once you account for time spent going through security, unless you have TSA pre-check.

I would be tempted to take the train in at least one direction simply because it is a pretty option on what is inevitably a travel day anyway.

If you don’t mind getting home late on Friday night, booking the Empire Builder is a viable option. This is especially true if you are traveling with a friend and can share the cost of a roomette.

Leaving a Certified LeSS Practitioner course early would be a problem as full attendance is required. Yet, leaving the conference slightly early makes a lot of sense if it saves a night’s hotel stay and if you don’t plan on going to SummerFest on Friday night.

La Crosse, WI

Outbound

*MSP;11:37am->2:57pm;MKE Empire Builder (coach:$43/first:$190) 3h20m
!*MSP;1:16pm->5:40pm;MKE Borealis (coach:$53/business:$107) 3h24m

Return

!*MKE;12:39pm->3;58pm;MSP Borealis(coach:$34/business:$72) 3h19m
*MKE;4:45pm->8:04pm;MSP Empire Builder (coach:$43/first:$341) 3h19m

Notes

The Borealis will be timely in both directions since it is a regional route which travels back and forth between MSP and CHI.

The Empire Builder is likely to be delayed going to Milwaukee since it originates on the west coast. On the return, the Empire Builder should be timely since it originates nearby in Chicago.

American Airlines has flights out of LSE to MKE, but they all connect through ORD and cost at least $618 round-trip.

Driving from La Crosse, WI to Milwaukee, WI only takes 3h10m.

Exclamation indicated route pricing example:

Outbound: coach: $53, business: $107 Return: coach: $34, business: $72

Summary

Amtrak is a fantastic option for anyone coming from La Crosse, and a far better option than flying. The other great choice is to drive.

Detroit, MI

Outbound

!*DET;6:26am->CHI->12:34pm;MKE Wolverine(coach/business)/Borealis(coach/business) 6h8m
DET;6:26am->CHI->4:44pm;MKE Wolverine(coach/business)/Hiawatha(coach) 10h18m
*DET;9:35am->CHI->5:08pm;MKE Wolverine(coach/business)/Hiawatha(coach) 9h10m

Return

MKE;8:05am->CHI->8:40pm;DET Hiawatha(coach)/Wolverine(coach/business) 12h35m
!*MKE;11:00am->CHI->8:40pm;DET Hiawatha(coach)/Wolverine(coach/business) 9h40m
*MKE;3:00pm->CHI->12:10am;DET Hiawatha(coach)/Wolverine(coach/business) 9h10m

Notes

All of these are regional routes which should be rather timely, and economical.

Delta has multiple 1h13m non-stop flights between DTW and MKE. A round-trip coach flight is $569.

Exclamation indicated route pricing example:

Outbound: coach: $97, business: Sold Out
Return: coach: $139; business $174

Summary

A business class seat on Amtrak is a reasonable low stress option compared to flying which saves some money. Flying is definitely quicker.

Grand Rapids, MI

Outbound

!*GRR;6:00am->CHI->12:34pm;MKE Pere Marquette(coach/business)/Borealis(coach/business) 7h34m

Return

!*MKE;3:00pm->CHI->11:34pm;GRR Borealis(coach/business)/Pere Marquette(coach/business) 7h34m

Notes

Regional route, so should be timely.

Although you need to connect in ORD or CLT, the prices to fly from GRR to MKE are very reasonable with prices as low as $236 round-trip and trip times as low as 3h29m.

Exclamation indicated route pricing example:

Outbound: coach: $67, business: $107
Return: coach: $71, business: Sold Out

Summary

Flying and Amtrak both work reasonably well from Grand Rapids. Flying is quicker, but a little more stressful. Amtrak is slower but likely less stressful as long as the trains run on time.

Cleveland, OH

Outbound

CLE;2:59am->CHI->12:34pm;MKE Capitol Limited/Borealis(coach:$127/first:$534) 10h35m
!*CLE;4:03am->CHI->2:34pm;MKE Lake Shore Limited/Hiawatha (coach:$127/first:$499) 11:31m

Return

Using Friday prices instead of Saturday prices:

MKE;3:00pm->CHI->1:45am;CLE Hiawatha/Capitol Limited (coach:$154/first:$494) 9h45m
MKE;3:00pm->CHI->5:38am;CLE Hiawatha/Lake Shore Limited (coach:$154/first:$394) 13h38m
MKE;3:00pm->CHI->5:38am;CLE Hiawatha/Lake Shore Limited (coach:$158/first:$399) 13h38m
!*MKE;5:45pm->CHI->5:38am;CLE Borealis/Lake Shore Limited (coach:$158/first:$499) 13h38m

Summary

There isn’t a direct flight between CLE and MKE, yet with a connection the flight time is only 3 hours and costs ~$550 round-trip.

If you are traveling with a friend you are comforable sharing a Roomette with, returning on the Lake Shore Limited could be fun. The sun would have come up by the time you get back home.

For at least the outbound, I would seriously consider flying. Amtrak’s embarkation time when departing CLE is just way too early in the morning.

Saint Louis, MO

Outbound

Sundays prices:

STL;4:30am->CHI->12:34pm;MKE Lincoln Service/Borealis (coach:$78, business: $125) 8h4m
*STL;6:35am->CHI->2:34pm;MKE Lincoln Service/Hiawatha (coach:$99, business: SoldOut) 7h59m
!*STL;9:40am->CHI->6:45pm;MKE Texas Eagle/Hiawatha (coach:$99, first: $458) 9h5m

Return

Saturday prices:

MKE;6:15am->CHI->2:51pm Hiawatha/Lincoln Service Missouri (coach: $72, business: $128) 8h36m
MKE;8:05am->CHI->7:07pm Hiawatha/Texas Eagle (coach: $99, first: $463) 11h2m
!*MKE;11:00am->CHI->7:07pm Hiawatha/Texas Eagle (coach: $90, first: $460) 8h7m
!*MKE;3:00pm->CHI->10:23pm Hiawatha/Lincoln Service (coach: $64, business: $103) 7h23m
MKE;3:00pm->CHI->12:90am Hiawatha/Lincoln Service (coach: $64, business: $103) 9h9m

Notes

Southwest airlines has a non-stop 1h15m coach only flight from STL to MKE for $673 round-trip.

The Amtrak route from STL to CHI only takes about 5 hours, and would make sense on its own. Once you add the connection to the Hiawatha in CHI, a trip on Amtrak starts to get rather long without saving any money.

Summary

Amtrak is workable from Saint Louis, but flying non-stop on Southwest to MKE airport is a better option in both directions.

Indianapolis, IN

Outbound

You can get from Indianapolis to Chicago on the Amtrak Cardinal, but the Cardinal only runs a few days a week. As luck would have it, the timing doesn’t work for traveling from IND to MKE on Sunday before the training, or on Wednesday before the UnConference. At least not without spending an extra day in either Milwaukee or Chicago. If you had family in either city this could work, but otherwise not.

Return

The return is somewhat better, but still not great as it arrives at midnight.

MKE;3:00pm->CHI->11:49pm;IND Hiawatha/Cardinal (coach: $71, first: $259) 7h49m

Notes

There is no non-stop flight option from IND to MKE. After connecting, better flight options cost $576 round-trip and take around 3 hours. If you count loading, and unloading times, the train isn’t all that bad.

There are lots of non-stop flights between IND and ORD. This will require a rental car or other ground transportation. The flights cost ~$430 round-trip and take 1h16m each way. The drive time from ORD to downtown Milwaukee is about 1h20m, plus the time it takes to get a rental car. Car service costs ~$250 each way, and takes about 1h15m curb to curb.

Driving from Indianapolis to Milwaukee takes 4 hours if you avoid rush hour traffic in Chicago. If your timing is bad and you pass through Chicago during rush hour, you can expect a total drive time closer to 5 or 6 hours.

Summary

There is no obvious best choice when coming from Indianapolis. Every option has problems, especially Amtrak.