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How To Do Chicago on a Whim

There are two ways to travel. One way is to plan and book months in advance. This usually means that you can get reservations at at least a couple of really hot restaurants, get tickets to popular shows and show up knowing exactly what you are going to be doing for the next few days. I have a certain admiration for people who are this organized.

Then there is MY way, which is to look over at each other on a Thursday night and say "hey, do you have to work this weekend?" and then spend the next few hours on Expedia looking for the best deal for air/hotel from Friday to Monday. What starts as a desire to fly to Mexico City for the weekend, ends up with me pulling the trigger on a combo that includes non stop flight with AA and three nights at the tony, boutique hotel, The James for $620 Canadian each. The hotel, alone, would have run us over $1000 CD for three nights so it was almost like they threw the flight in for free!

Okay, so we now have a flight booked and a place to stay for three nights so, worst case scenario is that we get there, we have a great hotel and we spend the weekend walking around, eating Shake Shack and drinking wine from Trader Joe up in our beautiful room, right?

My dream was to dine at Topolobampo one night, Alinea another and take in a Saturday night show at Second City. The reality of last minute travel is quite a bit different and getting into any of these venues is only going to happen if I am dining with Obama because mere mortals are never getting into any of these spots without reservations made way in advance. To travel on a whim like this forces us to work a little harder to find the hidden gems that tourists might not always find on their own and you either thrive on that challenge or you don't.

It's character building.

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Where we stayed:

The James
Expensive boutique hotels like The James are often featured in cheap bundles on sites like Expedia

I can't say enough about how nice The James is and I will absolutely try to stay there again - modern, bright, understated but attentive service with a lovely bar, newly redecorated common areas, a spa and a work out room for those who want to waste valuable Chicago time on a treadmill instead of running along the river walk. Reserve one of their bikes for the morning and they will have them waiting for you, free of charge. Sadly, we didn't inquire about this until our final morning and all the bikes were spoken for but we spent two days bombing around on Divvy (Chicago's bike share program) bikes. Oh, and a 3pm check out time!!! no cajoling, extra charges and guilt over wanting to hang onto our bazillion dollar room for a few more hours so that we don't have to rush to pack, check out and leave our bags with the concierge until we leave for the airport.

The hotel is right across the street from a Trader Joe, around the corner from Eataly, Starbucks and Shake Shack so, basically, in the cradle of YumYum heaven. The only thing that was missing was, perhaps, a nice Rick Bayless restaurant but even if there was one there, we would have never gotten in since we are just too, damned spontaneous. Since we almost never book trips more than a week or so in advance, we have gotten used to the fact that the most we can hope for as far as these hot restaurants go, is a spot at the bar if we go line up right before they open.

Luckily, Chicago is a great walking city with a vibrant downtown and lots of safe, interesting neighbourhoods to explore just outside of the downtown core, making it a great choice for an impromptu getaway. We were both constantly reminded of Toronto while we were there as it seems to be about the same size and many of the neighbourhoods looked like Toronto neighbourhoods. Armed with comfortable shoes, a Metro Pass and a 24 hour Divvy pass for two bikes, you can't help but have a great time.

Get a Metro Pass:

You can get one ride at a time for $2.25, a one day pass for $10 or a three day pass for $20. The trains are easy to navigate and will take you anywhere you want to go. Since we flew with just a carry on, we grabbed the L train from the airport with our day pass. A cab will run you around $45 and according to google maps, it was going to be faster to take the train than a car. It was easy to find and it only took about half an hour to get us a few blocks from our hotel. I wouldn't want to do this with big bags but you are only there for a long weekend so you don't need anything other than a rolling carry on and a knapsack, at the very most.

Take the architecture cruise

The best way to see the skyline is by boat
There are tons of cruises along the river and Lake Michigan but this is the only cruise that is affiliated with the Chicago Architecture Institute. Each one is hosted by a knowledgable volunteer docent who will regale you with lots of information about each of the important skyscrapers that form the famous Chicago skyline. The 90 minute tour is crammed full and we both loved it. I do not hesitate to recommend it and although it's not the cheapest river tour, it's well worth every penny. May I recommend either taking an early morning or late afternoon tour so you can take advantage of the light dancing off the glass buildings?

Cocktail Time

Smith and Wollensky is one of the many restaurants with patios along the river

Can't get onto the rooftop bar at Tanta, the trendy new Peruvian hot spot?

There are less popular places that have beautiful, outdoor patios like this one at Smith and Wollensky in the Loop. It's right on the river and although the food is a bit too old school chop house for my liking, it's a great spot to have a glass of prosecco, some oysters and enjoy a beautiful evening without having to worry about lineups, what you are wearing and whether you are still are cool enough. I am just talking about this place because that is where we went, but there are lots of other places to choose that sit along the riverfront. Just go walk until you find a place with free tables.

half priced martinis during happy hour make everybody happy

Or, if you don't want to sit outside, have a cocktail at the kitschy Redhead Piano Lounge instead - martinis are half price during happy hour, the piano lady managed to segue from Fly Me To The Moon into a bouncy, lounge version of Enter Sandman without batting an eye and I have a feeling that if we stayed a bit later, there would be dancing and background vocals supplied by the clientele. Points for not redecorating since 1967.

Spend an afternoon exploring the newly trendy Wicker Park

Hop on the blue line, get off at Damen and walk directly across the street to Dove's Luncheonette. If there is a line up to get in, and I think there will be, check in, give them your cell phone number and go for a little stroll - don't go too far because they will send you a text when a table comes up and you don't want to have to sprint back to the restaurant like we did. 70's blues was blasting from the jukebox, man buns and handlebar moustaches surrounded us while we all waited to dine on Southern tinged Tex Mex delicacies like Corozones de Palmas, Fried Green Tomatoes, Chili Cordero and Brisket Taco Norteno or Fried Chicken.

I had the Pozole Rojo, Shack had the Burnt Ends Hash and I forced him to join me in a Tres Palomitas - a shot of mescal, a shot of sangrita followed by a small glass of beer. No better way to start the afternoon. Run across the street to grab a designer donut from Stan's before setting off to explore the neighbourhood that is full of great cafes, bars and stores.

Catch a comedy show

You can't come to Chicago, home of Second City, without doing this. Last minute Second City bookings are not always easy to come by but there are plenty of other great comedy clubs to choose from. We went to the 10pm "Dirty Show" at the Laugh Factory and it was not all that dirty and very, very funny. Most places have a two drink minimum but that drink doesn't have to be alcohol so figure that into your budget. We found lots of small clubs to choose from that had tickets left on the same day so even if you leave it to the last minute, you will find a show at one of them.

Check out Chinatown 

We have a number of huge Chinatowns here in Toronto but that didn't stop us from checking out Chicago's smaller version and grabbing a steaming bowl of Mapo Tofu at Sze Chuan Cuisine after watching Anthony Bourdin swoon over the stuff.  The bowl of Mapo Tofu is big enough to serve a few people - even after eating a good size amount of it, the bowl looked like nobody had been within ten feet of it. Spicy, delicious and made both of our mouths beautifully numb.

Rent bikes from the local bike share - Divvy 

You can really cover a lot of ground on bikes and even if you are afraid of riding in traffic, you can spend a whole day going up and down the bike paths along the lake

We downloaded the Chicago Bikes app to help us locate bike docks all over the city. Its $9.95 for a 24 hour pass that allows you to rent bikes from any Divvy dock in the city. It's meant to get you from place to place, not to take it out and about for day long, non stop rides so just remember that you MUST dock it every 30 minutes and get another code from the machine and take it back out again to avoid extra charges. You grab a bike at Michigan and Rush and E Superior and ride it down to the Museum of Contemporary Art, dock it and when you are done and want to go back uptown, grab another bike and off you go. Chicago is pretty flat, easy to navigate it's grid style street layout and although it's not the most bike friendly city, it was lovely to cycle along the lake on the trails and you can always take the side roads in the city if you are a bit nervous.

Spend some time at Millennium Park

Of course you are going to swing by Millennium Park, see the Bean and check out of the beautiful Frank Gehry designed stage. We were there for Memorial Day weekend and so the park was packed full of people camped out on the grass in front of the amphitheatre where a free concert and dance party was underway. There are places to buy beer, get some snacks or you can bring your own - make sure to check the schedule to see if there are any scheduled concerts or events going on while you are there. There is also a mini golf and a great play area if you are bringing kids along. If it's too hot out or you find yourself dealing with a rainy day, you can visit the Art Institute of Chicago while you are down there. It's huge and has an amazing collection and is the best of all of the museums in the city.

Endless offerings from food trucks, donut shops like Stan's, Garret's for the famous "Chicago Style" popcorn (half cheddar/half caramel corn)

Okay, there is street food available but you might want to eat something a bit more civilized so pop by The Gage. We went for brunch and were pleasantly surprised to see two of our favourite Canadian items on the menu - a Bloody Caesar and Poutine. I am pleased to report that both dishes were proper and delicious. The Caesar contained horseradish but could have used a spiced rim on the glass - still, it was delicious and a great foil to the rich, cider braised pork shoulder poutine that was also full of bonafide cheese curds. I saw plenty of places that claimed to serve poutine which we all know is NOT a dish of fries covered in grated mozzarella and gravy. The Gage has a nice patio, a sumptuous, rich decor and the prices are very good. Shack's burger was deemed the juiciest he has ever had and my tasty chilaquiles were so filling that I could barely finish 1/3 of it, especially after the poutine.

The Gage
Look for neighbourhood restaurants that are full of locals


You might not be able to get into the newest places with rock star chefs but that doesn't mean you can't have great meals. There are endless restaurants that might not be found on the Timeout list of great Chicago restaurants but we are never let down by using our spidey senses. Look for places that are always crowded, read the menus before going in and try to look at what people are eating before you pull the trigger and get a table for yourself.

We walked by Quartino about ten times by dinner  on Saturday so Shack made me do a bit of a google to see if it was a tourist trap or not. When it sounded like it might be legit, we strolled down the street to check it out. Much to our surprise, the patio was overflowing and there was a line up for both the patio and to sit inside. Luckily, we snagged a small table upstairs and where whisked in pretty quickly. The room was packed full of locals, judging by the distinct Chicagoan accents, large, boisterous parties of revelers celebrating bachelorettes and birthdays, the food smelled delicious and everyone was happily tucking in to never ending plates of food.

We shared a thin crust pizza (I am sorry but this lasagna with a crust that calls itself deep dish pizza is not our thing- i hope we are allowed back after admitting that), a beet salad, meatballs in marinara and a caprese salad - in other words, old school American Italian classics with a few modern touches here and there- with a glass of prosecco. The food was quite good and although not earth shattering, it certainly hit the spot and set the tone for a fun evening out.

When you are out and about, catching a comedy show or watching a band along side college students and their moms, don't hesitate to follow the drunk people to the local taco joint for a late night nosh. Even the worst Chicago taco is probably going to better than what you get at home and we were very happy with our $20 spread at Taco and Burrito Palace #2 . We got six GIANT tacos and the largest serving guacamole I have ever seen and, again, could barely eat half of it, expecting the normal, little taco instead of these behemoth monster tacos. It wasn't one of the places on my list of tacos to try but it was right down the street from Kingston Mines , a popular live music venue that we popped into for a short set by Lil Ed and the Blues Imperials. If you are going to go the full fast food route, I suggest sticking to Shake Shack for great griddle burgers, fries and crazy ass custard shakes.

Shake Shack and Tacos from Taco Burrito Palace #2

Eataly here is a tiny version of the NYC Eataly but it has a great coffee counter, a sandwich counter and a small selection of Italian treats with wine for sale on the second floor. We grabbed our morning coffee here before venturing out to explore the city (for our early morning coffee, we did depend on Starbucks as Eataly didn't open until 8am and we like to get up early and enjoy the quiet before the city wakes up for work.

Chicago is wonderfully walkable

There are lots of other touristy things to do if you don't mind some line ups and there are certainly things that we couldn't fit in like a Frank Lloyd Wright tour , a trip up to the sky deck to sit in the glass box high above the city, visit the Art Institute of Chicago, catch a game at Wrigley Field, the Shedd Aquarium or the ride the ferris wheel at the Navy Pier and that just means that we will have to go back and maybe we will plan our next trip a bit more in advance.

Yeah, that's not going to happen.

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Helpful links:

Choose Chicago to see what's on while you are there
Chicago Architecture Foundation River Cruise
Smith and Wollensky
Redhead Piano Bar
Dove's Luncheonette
Laugh Factory
Sze Chuan Cuisine
Stan's Donuts
Divvy Bikes
Millennium Park
The Gage
Taco and Burrito Palace #2 
Kingston Mines

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