Sharing a review of my first trips to Chicago and Ireland that involved eight nights, eight flights , one carry-on suitcase and an adventurous attitude!
Tourism Ireland and Aer Lingus offered an opportunity for U.S. & Canadian agents to explore Ireland via 1 of 3 different six night motorcoach itineraries arranged by "Failte Ireland" National Tourism Development Authority. I chose to explore the southwest region of Ireland and needed to fly to Chicago a day prior to board an Aer-Lingus red-eye flight to Shannon, Ireland. This gave me an opportunity to visit Chicago one night before and one night after exploring Ireland.
My Chicago Introduction:
After my flight landed at O'Hare and with under 24 hours to explore Chicago, I considered the Blue Line train for the famous "EL" loop experience to downtown. Knowing there were multiple stops and transfers, I opted instead for Airport Express shuttle which stops at most downtown hotels. Airport Express had an easy check-in counter at the terminal and learned that Airport Express had walk out counters at most terminals in O'Hare and Midway Airports.
With clear 70 degree October weather, I enjoyed views from the shuttle at we headed downtown for our 45 minute trek. We made good travel time for late afternoon traffic without any car pool lanes. My first night's destination was The Marriott Chicago Downtown on Michigan Avenue (AKA Magnificent Mile) known as the main shopping, dining and action street in downtown Chicago. I quickly found out that the reason that the lobby sports bar was packed on a Tuesday night was due to multiple conventions at this bustling Marriott. After a quick check-in and stop at the concierge's desk for local map, I zipped up to my 29th floor room. My accommodations were roomy and contemporary. It was a treat to see the tops of buildings and Lake Michigan views from my windows. After soaking up the scenery from above, I headed below and started my 5 block trek to shore's edge to catch twilight over Lake Michigan and watch the dancing flumes of water at the fountain outside of historical Navy Pier, Chicago's favorite playground. Navy Pier offers a myriad of activities of shops, restaurants, an IMAX theatre, amusement park with giant ferris wheel, boat tours for hire, a Shakespeare Theatre, Chicago Children's Museum, the Amazing Chicago's Funhouse Maze, The Smith Stained Glass Museum (the only one of it's kind in the U.S ) and much more. From segways, to surreys and bikes rentals, there is something for everyone. From the pier, I headed back to Michigan Avenue to the old Chicago Tribune Building to watch WGN radio DJs broadcast live from the Showcase Studio. My evening ended with a moonlight stroll along the Chicago River that flows in from Lake Michigan before heading back for some jet lag slumber.
The next morning, with luggage in storage, I was picked up by Grayline/American Sightseeing for my 4 hour "Grand Tour" of 
Northern and Southern Chicago. (This tour can be broken into two hour segments and taken on different days). The Grand Tour included views of major buildings like the Sears Tower and John Hancock Observatory, suburbs, parks, museums, and offered history of early to present-day Chicago. Our tour included a visit to Lincoln Park Conservatory and Zoo, photo-stops, a drive-by of Oprah, Barack and Mayor Daley's houses, a view of every major park and city area and Cub's famous Wrigley Field. Close to the end of our tour, we stopped at Alder Planetarium for a picturesque downtown skyline and lake view. From that vantage point, I kept struggling with the fact that I was looking at Lake Michigan and not an ocean due to its size. Harder yet to imagine parts of it freezing over in the winter.
My afternoon transfer to O'Hare's Int'l Terminal #5 for Aer Lingus took 45 minutes. Once inside Terminal 5, I was not prepared for the instant congestion of downstairs travelers in a narrow hallway working forward towards multiple security lines, a few eateries and shops prior to heading to " departure gate land" upstairs.
Thankfully, there were long hallways upstairs for walking and a display of photographs showing Chicago's history along the waterfront to pass the time before boarding my 7 1/2 hour flight to Shannon.