Chicago, IL to Winona, MN

Trip # H

Chicago, And, Oh Yeah, Biking Most of the Way to Minneapolis

August 22, 1984 to September 2, 1984

367 miles to Winona, MN

Route is approximate. No historical documentation exists to substantiate the exact route.


I finished graduate school in May 1984, but was one of the few class members that did not have a job by graduation. I was glad to get back to Washington, D.C., but was pretty poor. I was living with my best friend in Shaw, rent free, and using the Adams National Bank ATMs' because they dispensed $5 bills, my spending limit that summer. I was un-employed, totally bummed, and psyching myself out most of the summer.

I finally landed a job with the Kenneth H. Michael Companies in Cheverly, MD in August. This proved to be a boon. It was a small company with a small staff. I learned everything from permitting to construction to leasing to dirt work while I was there. To celebrate getting my new job, I decided to bike from Chicago to Minneapolis. I had never been to either city, and still had the long distance biking itch from my 1979 and 1980 bike trips.

Pack rat that I am, this is probably one of the more difficult trips to re-create from the scraps and receipts I usually hole away.

I also was completely fascinated by my first visit to Chicago, and just drank it in. My first true "big city tour" with history, architecture, grand urban design, dense urban transit, and a bike path. It was heaven.

Chicago, Chicago. City of Broad Shoulders.

My ticket says that on August 22, 1984, I flew from Washington National to Chicago via Piedmont Airlines. Somehow I found cheap housing in the University of Chicago dorms on the south side of Chicago. I rode my bike from Chicago O'Hare to the Univeristy of Chicago. That was quite a challenge for the first day of a trip: exiting the airport, getting oriented to a strange city, riding and reading a map, finding my way.

During the following days, I just absorbed Chicago. Lock, stock and barrel. Gladly drinking from the firehose. My stay in Chicago included:

  • Touring the Robie House, my first Frank Lloyd Wright home and my introduction to the architect and his work. The Robie House happened to be right down the street from my dorm room.

  • Riding the El and seeing the Loop for the first time.
  • Taking the Green Line Elevated back to University of Chicago that first night. Pulling out of the last stop on the Loop before heading south, the train operator looked back at me in the rear view, asking with his eyes, "Are you sure you want to be on this train???" I remember seeing fires burning in barrels, and empty blocks, and groups of men huddled in the dark. I was a little scared walking from the El stop to my dorm.
  • Taking a commuter train from downtown to the University of Chicago the next evening, and noticing private security guards on the U of C station platform.

  • Exploring the Burlington Railroad Zephyr streamlined train exhibit at the Museum of Science and Industry.
  • I have a brochure on, but don't remember going to, the top of the Sears Tower.
  • Visiting the Chicago Board of Trade.
  • Taking a Chicago River boat tour.

  • Understanding the City of Broad Shoulders' huge townhomes and the broad brown brick vernacular architecture.
  • Vacuuming up the downtown Chicago architecture. Chicago was where the skyscraper was invented.
  • Checking out the architecture and interior of both the Marshall Fields and Carson Pirie Scott Department Stores.

  • Exploring the Southside Chicago historic district. After the Chicago fire, this was one of the richest neighborhoods in the city. Now it is a warehouse district. Somehow the Glessner House and a few others survived.
  • Attending the Degas exhibit at the Art Institute of Chicago.

  • Photo from the "Chicago Landmarks" website.

  • Touring Pullman, the Pulman Parlor Car Company town in the area south of Chicago.

  • Photo from the "Chicago Historical Society" website.

    Chicago Explorations

    Heading Out for Wisconsin and the Twin Cities

    I don't know when I left Chicago, but I headed north on the Lake Shore Drive bike path, following it to its end, and then rode through the "comfortable" neighborhoods of the North Shore. I remember passing by Racine (and missing the Johnson Wax Headquarters building by Frank Lloyd Wright) and riding through Kenosha, Wisconsin. I had my first cheddar brots in Milwaukee and spent some time exploring downtown and some of the urban renewal projects there.

    I remember getting a warning ticket for going the wrong way on a one way bike street in Madison. WOW. I had never seen a bike street, much less gotten pulled over for improper bike riding.

    I remember a long hot sunny day riding through miles and miles of corn fields, and no shade.

    I remember arriving at Prairie du Chien. Like, Kenosha, I knew nothing about, other that it had an interesting place name I was familiar with, and was now in it.

    I remember the excitement of arriving at the Mississippi River and camping in a campground next to it. That excitement turned to frustration when I discovered being next to the Mississippi meant ten million mosquitos. Since I only had a fly (and not a tent with netting), after many fruitless hours wrapping my head in shirts and multiple dousings of bug repellant, I found a bench in the Men's Room and finally fell asleep. (The restroom windows had screens thank goodness!)

    I was running out of time, so I Amtrak'ed the last segment of the trip into Minneapolis. I picked up the train in Winona.

    In Minneapolis, I explored the IDS center, Nicollette Mall, and the skybridge system, all well known and innovative urban planning schemes at the time.

    I remember a long and rather complex bike from where ever I was staying in downtown Minneapolis to the MSP Airport. My ticket says I flew from Minneapolis to Chicago to National via American on September 2, 1984.


    I was just facinated with Chicago and learning about its history, commercial architecture, neighborhoods, transit systems, vernacular residential architecture, and everything else. A primo trip, even if biking played second fiddle.

    Last Update: Mar 5, 2008