Chicago: Fast Times in the Windy City

To get from Toronto to Chicago involved 2 buses, numerous stops, an intrusive border crossing experience and a whole lot of time.

I always dread having to cross into the US, especially by land. The US Border Guards are pretty much always nasty and incredibly self-important at the best of times, but the guy that was working on the border in Detroit was an even worse piece of work than usual.

He was so supremely rude to everyone, even including the US citizens, and the whole experience made me feel like a criminal. He was also really creepy and gave you the feeling he was undressing you with his eyes – creepy!

Anyway, after that unpleasantness we had 1 ½ hours in Detroit (more unpleasantness) before catching our bus to Chicago.

Detroit has a really weird, post-apocalyptic feel about it. I saw it described that way in an article and it really does describe it perfectly. It was a beautiful sunny day and the modern skyscrapers sparkled in the sun.

What made it weird was that there were hardly any cars or people about. It literally felt abandoned which was kind of spooky.

We had to catch our bus from the Rosa Parks Transit Centre, about 15 minutes walk from the Greyhound Station. It took another 6 hours to get to Chicago from Detroit with a meal break along the way.

The difference between the US and Canada is remarkably pronounced and I always feel a bit out of place in the U.S., while I feel more in-sync with Canada. Other than the people, I think one of the massive differences is that the U.S. is a lot more consumer driven.

Along the highway to Chicago, there were billboards everywhere for a dizzying array of useless products and fast food chains, including far too many for Personal Injury Lawyers.

Trav and I were both very excited about getting to Chicago. After reading numerous articles, watching it featured in movies, TV and travel shows – we were finally going there! 

After pulling up to the Megabus stop downtown, we were exhausted after 12+ hours of travelling.

And it wasn’t over yet.

We struggled to find a bank that was open to draw some US dollars, finally having to use a Hotel ATM. We hopped onto the L (Chicago’s train system) to get to our couch surfing Host Liz’s place, in the Lincoln Square neighborhood north of the city.

Because it was fairly late in the evening at this stage, the train took a long time to arrive and was very slow.

Despite worrying about how late we were going to be getting to Liz’s (and no way to contact her with only a Canadian SIM card), I enjoyed trundling along, weaving between the buildings.

The tracks are elevated and it reminded me of the Highline Park in New York, peeping into offices and people’s apartments (spying on people is fun).

After the train turning into an express without warning (well, no warning that we were aware of), we passed our station without stopping so we had to get another train going back in the other direction, which took over 15 minutes to arrive.

We didn’t end up getting to Liz’s place until 11pm, apologising profusely for how late we were. Luckily Liz is a lovely lady and very laid back.

We sat with Liz, her vocal and pudgy cat Mina and one of her friends that came around, talking until past midnight. Liz has a fantastic walk-up apartment in a beautiful green neighbourhood with a happening main street. We even got our own room!

We had four days to explore Chicago and there was so much that we wanted to see (and eat) that we rushed around trying to do it all (this is a theme with me). We had such a fantastic time despite the fast pace and Chicago was everything I imagined it to be, and more. 

Chicago should be right up there with New York and LA on everyone’s USA Bucket List, because it is just an amazing city.

If you don’t have four days to explore Chicago like we did, you can get a food overview of the city by spending two days in Chicago – it’s the perfect destination for a weekend break.

Chicago has a fascinating history, lots of sandy lake beaches, incredible food and the architecture is, in my opinion, unmatched by any other Northern American City.

I am not an architecture fiend by any means but Chicago can make anyone sit up and take notice. There is a perfect mixture of intricate Gothic and Neoclassical buildings alongside modern glass skyscrapers.

Trav and I did a self-guided Architecture Tour – there are a lot of great guided Architecture tours too – and my favourite buildings were the Gothic Tribune Tower and Frank Lloyd Wright’s The Rookery.

The Tribune Tower is a very interesting building because as well as being beautiful, if you look closely at street level you will see that it incorporates fragments of other famous buildings and sites from around the world.

There is a hunk of the Great Pyramids of Giza, Westminster Abbey, Great Wall of China, Berlin Wall and Angkor Wat among others. Not sure how they got their hands on these priceless particles, but I would think that it probably wasn’t done in a legal manner.

Before our Architecture appreciation tour, Trav and I fueled up at a Chicago landmark near the beginning of the iconic Route 66: Lou Mitchell’s Diner. This is a great place for all day breakfasts, popular with tourists and locals and first of our many food highlights in Chicago.

We visited the end of Route 66 when we were in LA a few years ago so it felt only right to see the beginning.

Our favourite Chicago food experience was trying the famous Chicago style Deep dish pizza for the first time. Liz, our couch surfing host, recommended going to Pizzeria Due which is the second restaurant from the man who invented the Deep dish and it has been open since the 1950s. It is a cosy little place with a nice ambience.

Once you order the pizza you want, you have to then wait 40 minutes to 1 hour for it to be ready because all of their pizzas are made from scratch to order. It was certainly worth the wait!

The base is thick and buttery, more like a quiche crust than a traditional doughy pizza base. We just had a simple cheese pizza but the ingredients were so fresh and tasty and we just loved it.

We ended up going back to Due a couple of nights later for round two. We got a broccoli and pesto pizza with three cheeses this time around and it was even better. I am quite sad not knowing when I will be able to have Deep dish pizza again, it was a food revelation.

Liz also told us about a great pie place in the Ukrainian Village neighbourhood, west of the loop (downtown). It took us over an hour to get there but they do have some amazing pie. We shared slices of Cherry Berry and Banana Cream which were both so damn good!

Another unique Chicago treat are the Chicago hot dogs which are ‘dragged through the garden’. They are served on a poppyseed bun and come with salad ingredients and a pickle. I could have spent WEEKS or MONTHS exploring the Chicago food scene (don’t even get me started about the amazing selection of cheap craft beer!).

We only had the money to do more of the street food and cheap restaurant options but even at that level, the quality was great (deliciously so).

Other than the architecture and the food, I would say that my other two favorite aspects of Chicago are the numerous beaches and the friendliness of the people. We noticed straight away that although Chicago is a fast paced, massive city, it was a lot friendlier than its biggest rival: New York.

I liked New York but I did find the in-your-face rudeness and aggressive attitude of a number of the residents to be intimidating, especially after living in London for so many years. London can also be rude but in a way more passive aggressive (evil eyes and heavy sighs) kinda way.

So many people started conversations with us in the street and on the El while we were in Chicago. It was usually when we had all of our bags with us (great conversation starter) or when we were being obvious tourists, looking at maps/guidebooks or taking photos.

Restaurant service was also better and the whole city felt a lot more relaxed than New York did, and more welcoming to tourists.

We were offered a free lunch one day, no strings attached, at a Middle Eastern Restaurant that was opening. It was delicious and the owner came out to thank everyone that came, he was so grateful and nice when we were the ones that got the free lunch.

I read somewhere that Chicago has more city beaches than any other city in the US. Not sure if this is true but it sure does have a lot. I had thought that after swimming in Lake Ontario while we were in Toronto, that Lake Michigan would be even colder as it is larger.

That was not the case at all and we spent a lot of time swimming at the various beaches to escape the stifling humidity.

The largest beach that we visited was North Street Beach which had a LA/Surfers Paradise feel to it which I wasn’t too fond of. It was way too crowded and there were too many frat boy types getting drunk and being obnoxious.

My favourite beach was 12^th Street Beach. We visited there the day that Phish were playing at the outdoor concert venue right next to the beach so we got to hear them playing for free while we cooled off in the crystal clear and strangely cooler water.

Chicago has some great parks too. Millennium Park is right by the water and has a wildflower garden, the famous silver kidney bean shaped sculpture that reflects some crazy images and the interactive Crown fountain, two big pillars that cascade water and project images.

Grant Park was hosting the Taste of Chicago Festival while we were there and it is also home to the giant Buckingham fountain, which featured in the intro for ‘Married with Children’.

Lincoln Park is the biggest Chicago park at 1200 acres and is also set on the waterfront of Lake Michigan. A great place for a wander and we went swimming off the rocks.

The mafia and crime history in Chicago is intriguing, after all this is where Al Capone ruled with an iron fist. The Greenmill Jazz Club used to be frequented by Al and his henchmen, with Al entering the club by underground tunnels to elude authorities.

We visited the spot where the famous St Valentine’s Day Massacre occurred. Al’s men shot and killed seven of Bugs Moran’s guys in front of a garage. The garage was pulled down in 1967 and the site is just a parking lot now.

We also saw the theatre that John Dillinger was killed outside by the Police, trying to escape being captured.

A lot of exciting stuff has happened in Chicago over the years!

We aren’t really into big nights out on our travels, usually preferring to be up early to explore followed by a reasonably early night, ready for the next day.

We bucked that trend a bit in Chicago. We still got up early every day but we also had a couple of evenings out.

Our second night we caught the sunset from the 96^th floor of the Hancock Tower. It is only the third tallest building in Chicago but has a prime position right on the lake and the view only cost us a beer each as there is a lounge up there.

It was a great alternative to spending $18 to visit the Observation deck, which is two floors below.

Watching the sky change to various shades of pinks and purples to a dark sea of black, speckled with bright lights, was a definite Chicago highlight! The Ladies Washrooms actually had the best views and most people in there were there to take photos rather than use the facilities.

The famous Second City Comedy Company is located in Chicago and you can see the stars do Improv after their nightly show for FREE so we were all over that.

Second City is where lots of big Comedy names such as Tina Fey, Steve Carell, Mike Myers, Bill Murray, Jim and John Belushi, Dan Akroyd, Chris Farley and John Candy started out. We had to wait for about 20 minutes then were ushered in to take the seats vacated by people leaving.

They definitely missed out.

The Improv went on for about one hour and was hilarious. Improv can be awkward but these guys were super talented so it was so great.

Navy Pier is probably the most touristy place in Chicago. We turned a blind eye to the throngs of people and the cheesy chain restaurants like Jimmy Buffets Margaritaville (the worst of them all if you ask me) to go and see a more low key attraction on Navy Pier, the Stained Glass Museum.

The Museum was free and because I have always liked stained glass, we thought we should take a look.

There are some beautiful pieces there but the highlight for me were four Art Nouveau style panels, each with a beautiful woman representing a different season.

I was surprised to read that it is believed that one of my favourite artists, Alphonse Mucha, actually created them himself as he was living in Chicago at the time and they definitely represent his style.

Whether it was him or not, they were really beautiful and the museum was worth visiting just to see them.

Another thing that Chicago is famous for as well as its architecture and Deep dish pizza, is the Chicago Cubs. The Cubs are one of two Major League Baseball teams in Chicago, and one of the first in the US.

They are probably best known for their 104 year losing streak, giving them the nickname ‘the lovable losers’. They won the World Series two years in a row in 1907 and 1908 then something happened.

A lot of people believe that they were cursed.

There is a Tavern in Chicago called the Billy Goat Tavern. The Owner, Billy Sianis, took his pet billy goat to see a Cubs game in 1945 only to be turned away despite the goat having its own ticket (he was a quirky fellow).

Billy cursed the Cubs to never win a Championship at Wrigley Field again, and they haven’t (although they hadn’t at that stage for 37 years anyway).

We visited the Billy Goat Tavern for a look around. It is a bit of a dive but there have been so many famous faces and even Presidents (the first Bush and Obama) that have been here over the years so the Wall of Fame is definitely worth checking out, as are the crazy letters that Billy Sianis wrote.

The one that stood out to me was asking the US Government for permission to be the only food franchise on the moon (I told you, quirky).

After a two day camping trip in Michigan, we arrived back in Chicago for one night before we left the Midwest for the real West, the Pacific Northwest that is, flying via Minneapolis to coffee scented Seattle.

We both really enjoyed our time in the Midwest and I can’t wait to visit Chicago again for some more Deep dish pizza! It is such an elegant yet friendly City and I defy anyone not to fall in love with it like we did.

Budget busted and waistline expanded but it was allllll worth it.

If you liked this post, you should check out some of my other US content:

• Swimming with Wild Dolphins on the Big Island of Hawaii – for FREE!
• How to Spend the Perfect 3 Days in Denver
• Chilling Out on the North Shore Beaches of Oahu
• Why you Shouldn’t Miss the South Bay of Los Angeles
• Telluride: The Best Mountain Town in Colorado
• Impressions of the Garden Island: Hawaii
• Sitka: My Favorite Place in Alaska
• Juneau, in the Rain
• Discovering the Frontier Spirit in Talkeetna, Alaska
• Seaside Seward and Riding the Alaska Railroad
• How to Escape the Crowds in Waikiki
• How to Spend Three Days in Boston During Fall
• The Best Small Towns in Massachusetts
• Discovering the Understated Charms of Seattle
• Portrait of an Idyllic New England Island: Martha’s Vineyard