I’ve never made a trip to Chicago I didn’t like. Travelling by train and booking hotels on makes it an affordable and fun weekend trip. While visiting Chicago is always exciting, winter is a good time to enjoy indoor activities. During a recent trip we visited the Chicago Museum of Science and Industry – probably the most awesome museum in the country which we would’ve enjoyed more if it didn’t close at 4pm; saw a comedy show at the Second City, if you laugh non-stop when watching SNL you’ll probably love this one; saw a Broadway show American Idiot – I liked it a lot and I am not even a fan of Green Day, the first musical I’ve seen without an intermission; we took a tour of Chicago Pedway and walked for 90 minutes without getting out in the cold; went to the top of the John Hancock building – we didn’t use the skating rink but in case you were wondering – it’s small, lame and not even real ice. In between, we ate a lot of good food, walked around in the cold as much as we liked, saw a light show at the Millennium Park and even had time to visit relatives. And all of this in one short weekend. I’ve been to Chicago many times and never had to do the same thing twice or eat twice at the same place (unless I wanted to). There is a never-ending list of things to do, see and eat.

Unions have the best props

Chicago food trucks

Light show at the Millennium Park.

Michigan Ave.

View from the John Hancock Observatory. Willis (Sears) Tower is on the right.

View from the John Hancock Observatory

Art at the Millennium Park




  • I Travel for Jools

    I had always flown to Chicago before reading your first post about taking the train, but based on your recommendation, I took the train and haven’t flown there since.  I’ve now done it three times and each time was pleasant and on-time both ways.  Regarding Chicago itself, I couldn’t agree more.  It’s a fabulous city to visit, expensive, but worth it. 

    That said, Illinois is becoming a terrible place to live.  My sister lives west of Chicago and her property taxes are outrageous compared to ours and it’s even worse in the City.  Traffic is terrible and I don’t know if you’ve ever driven to the burbs from Chicago but half the time you’re on narrow two lane roads with impatient drivers and ungodly heavy traffic.  I have never been there that I haven’t come upon a horrific accident.  Recently one of my nephew’s in-laws was killed in a bad wreck so it’s definitely a place to strap on your seat belt.  And, of course, their political system is so corrupt, it’s legendary.

    But for a visit, it’s right up there as one of my favorites.  Great pics, Meesha.

  • We did go to suburbs but took the MetrA train and it was Saturday so it was not crowded at all. I like all the public transit there but it’s not cheap at all. My kid dreams about going to college there, it’s her favorite place to be. We too never went back to flying to Chicago, train can’t be beat on being comfortable and hassle-free.

  • Melinda

    Love Chicago.  We go every year in March or April for a conference and to see friends, and each time we stay at a different place in the city.  This year we’re renting a condo with friends so it’s super cheap and I can cook!  3 years ago we stayed on Michigan Ave. but on the south side, and the view of the city was fantastic – just like your pic!  Now I’m even more excited to go!

  • Nice pics; almost makes the place look livable. But the oversized rats are the truth of course…

    Also, this: “… if you laugh non-stop when watching SNL you’ll probably love this one.”?

    Hands down best backhanded compliment of the year. Well done.

  • Well, there is a non-zero number of people who think SNL is funny, this show is very similar. They had a good joke or two, but other people in the audience found it more hilarious than I did. I was expecting better from a place that is supposed to attract the best comedic talent in the country.