Weekend in Chicago: Getting there

Mrs. Miler, Tyler Miler, and I visited Chicago last weekend.  I don’t usually write trip reports, but I learned a few cool things that I want to share.  To keep it light, I’ll break up the trip report into four parts: 1) getting there; 2) lodging; 3) eating; and 4) stuff to do.

Chicago Photos
This photo of Chicago is courtesy of TripAdvisor


Amtrak runs the Wolverine line which travels between Michigan and Chicago.  The Amtrak station is conveniently close to my house, so it’s a great option.  Driving would be faster, but I really don’t enjoy navigating Chicago’s streets or paying steep parking rates.

Prior to our trip, I came close to buying Amtrak tickets for the three of us for $100 each, round trip.  Then I remembered that Amtrak is an Ultimate Rewards transfer partner.  So, I investigated the Amtrak Guest Rewards program.  I found that the Wolverine line was considered a “special route” and would cost only 1,000 points each way.

With that information in hand, I transferred 6000 points from Ultimate Rewards to Amtrak.  The transfer was free and instantaneous.  I then used the points online to buy the tickets we wanted.  It was all completely painless.  Even, better, I saved $300 by spending 6,000 points!  That’s a redemption rate of 5 cents per point.  I’ll take it!

Special Routes

In case you’re interested, here are the “special” routes:

Blue Water®, Wolverine®, Cascades®, Pacific Surfliner®, Capitol Corridor®, San Joaquin®, Hiawatha®, Downeaster®, The Lincoln Service®, Illini Service®, The Carl Sandburg®, Missouri River Runner, The Illinois Zephyr®, The Saluki®, The Hoosier State®, The Pere Marquette®, The Piedmont®, and The Heartland Flyer®.

While the Wolverine line is fine, its worth mentioning that I’ve ridden the Cascades line in the past from Seattle to Vancouver.  That was awesome!  It runs along the ocean much of the way, and the conductor even pointed out bald eagles a few times.


Coincidentally, the same day that we rode the train to Chicago, I received an email from Amtrak Guest Rewards with an update about their program.  As of April 1, point requirements are going up:

Click learn more to view adjusted redemption items.

Wow, that’s a shame!  I had just discovered the amazing value here and it was already being devalued!  Actually, it’s not that bad.  Even with the cost of the special routes increasing by 50%, they still deliver 3.33 cents per point value when compared to $100 round trip tickets.

However, if you want to take advantage of the current prices, you can book as much as 11 months out.  So, book now before the rates change!

Other Cheap Travel Options

For completeness, here are a few other options we could have used to get there cheaply:

  • MegaBus: $87 per person, round trip
  • American Airlines via British Airways Miles: If low level awards were available, we could have spent 9,000 British Airways miles (Avios) per person for round trip flights.
  • Spirit Airlines: $88 per person, round trip.

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About Greg The Frequent Miler

Greg is the owner, founder, and primary author of the Frequent Miler. He earns millions of points and miles each year, mostly without flying, and dedicates this blog to teaching others how to do the same.

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If you book way in advance with Megabus it is much cheaper! I am going to Chicago in mid May for a total of $20.50 Round Trip!Double decker bus, wifi is okay.

I burned 60k Amtrak points (from Continental and UR transfers) for this beauty:

4 business class seats Ann Arbor to Chicago
2 sleeper cabins on the Southwest Chief to Los Angeles
2 sleeper cabins to Seattle on the Coast Startlight

This trip will take 80k Amtrak points after April 1. Just a heads up.


gpapadop: Thanks for the megabus tip. We decided last minute to go to Chicago so the rates I listed were based on that. Your trip out west sounds awesome!

Pat O: I might see you there. We often go to Chicago for Memorial day weekend. Have you been to Chicago before? I’ll post soon some recommendations I have for stuff to do.

Pat O
Pat O

I’ll be there staying at the W lake shore hotel over memorial day weekend. We are using 18,000BA points and 14,000 spg + $60 for the 2 nights. Just looking for places to visit now!


Thanks for the reminder about the Amtrak devaluation. Megan and I have been meaning to take the Cascades route up to Vancouver during our last year in Seattle.


Hey you were in my city and didn’t call me? Just kidding, FM! I’m headed to Vancouver and Seattle in April and was originally going to drive from one city to the other. I saw this deal on Flyertalk a few weeks ago and booked business class Cascades tickets for 1500 UR points each! Such a deal, and even with the upcoming increase in points it is still a great deal.


FrequentMiler, that was a great redemption. Too bad about the devaluation, but 3.33 cpp is still a great value for domestic travel. Was the train ride pleasant?


G: Yep, great train ride!


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