We took an unabashedly-touristy, first-timers visit to Chicago recently. If you’d like to replicate our soooo-not-a-cool-kid (but still really fun!) trip, you can follow these steps below:
Day One:
Getting there:
Plan to take an after-work flight straight into Chicago in time to go out on the town. Realize the weather has different plans. Discover that if your flight is delayed by a few hours, DIA is a great place to get pumped for your weekend with an airport pub crawl…(Seriously – LOTS of good bar options for an airport). Go to lots of places, but discover you should have just parked it at Cru or Root Down all along for the best food and drinks.
Where to Stay:
Stay at the Hotel Monaco in downtown Chicago. It’s beautiful, modern, reasonably priced and conveniently located within walking distance to all of the main tourist attractions. Find out that all those rumors about Chicago being cold, rainy and windy are based on the truth and that your hotel is also in a district filled with lots of Lyft drivers. Arrive at your hotel at nearly 3 am. Fall into bed in a stupor.
Day Two:
What to eat:
It’s a tourist day! Get out your cute umbrella and walk towards the action. On your way, stop in at Le Pain Quotidien. Plan on ordering something reasonable. See a pastry that makes you feel giddy. Ask what it is. Hear it’s called a French Cream Donut – three of your favorite words! Discover it’s every bit as amazing as it looks. You’ll be walking a lot today, so don’t worry about the calories. Feel a little guilty when you find out that this place isn’t just a local bakery in Chicago. But also know that you would never have had this amazing marriage of a donut and a cream puff anywhere else. Come to terms with your guilt over not going somewhere only found in Chicago.
Do:
Seriously – take most of the day for this one. It’s amazing. So wander, contemplate, eavesdrop on pretentious sounding art conversations, take selfies with Whistler’s mother or Van Gogh. Wonder why the Renaissance had so many paintings of half eaten food items (did the painters get hungry and snack while staging their still life scenes?), remember that history and the Bible are both really gruesome, see all of those trips Dali posters from college dorm rooms as they were meant to be seen… see the whole museum and take your time. If you have any room after your giant cream filled donut, stop at the museum cafe for some extra caffeine and a snack or lunch.
Check out The Bean. It’s fun and touristy and obviously a must do and just across the street from the museum. Be sure to get pictures from all sides and underneath.
If you still have time, walk to Navy Pier. You can even take a ride out in the harbor. Chicago’s sparkling city skyline is breathtaking from the waterfront. If you think you can pass for twelve, play on the most seriously incredible playground in the world. Marvel at all the people out running, even though it’s cold, windy and rainy.
Eat Again:
Deep Dish pizza, of course – you are in Chicago, after all. Skip the crowded institutions and check out Labriola. Their crust is like food miracle – crispy, flavorful and a little chewy, even though it’s covered with cheese and sauce and toppings. Resist making a rookie mistake and eating all the bread before your pizza comes or you’ll be regretfully daydreaming about all the miracle crust pizza you didn’t finish weeks after your trip.
Day Three:
Eat:
Hotel restaurant brunch. When your hotel has a restaurant that comes up on the “Where to Eat in Chicago” lists, you may as well stay there for Brunch. Order the Bloody Mary – it’s peppery and amazing. And strong.
Do:
Sears/ Willis Tower:
Wake up and see that it’s still totally cloudy, but realize you bought tickets ahead of time and may as well go to the Sears/ Willis tower even if you might see nothing but clouds. Tell yourself that at least the clouds are beautiful and there are no lines. You’ll just have to come again.
Eat again:
Eat for an hour or two at Eataly. (I told you: unabashed wide-eyed tourism for this trip). Get a Nutella Crepe, or the hands-down-best Panini I’ve ever had in my whole life, or any number of amazing food offerings at one of the many options in the 63,000 feet homage to italian food and cooking. Yes, it has been compared to an IKEA, but it’s still fun. Especially if you happen into Chicago on a cold, windy, and rainy weekend that prevents wandering the streets to find more unusual fare. If you still feel a little bad about your lack of creative food adventuring, have another glass of wine. Or another Panini.
Get all dressed up and go out:
See a show at Second City: You may have suffered through your neighbor’s improv performances back home, but this is the real deal. It was hilarious and fresh and professional. And they keep the drinks coming.
When it’s over, go next door for Karaoke at 1959 Kitchen and Bar. We saw a couple of the performers there from the show and lots and lots of audience members who now felt ready to perform. You could too: Order lots of drinks. Unsuccessfully try to convince your partner to sing 90s hits with you. Pout (and thank them the next day for their steadfast resistance). Decide to go somewhere else. Stumble around and find an open restaurant nearby. Have amazing tacos. Be amazed that Chicago has such good tacos. Sadly discover the next day that said taco restaurant is from Texas and so you have found yet another imported restaurant that amazed you while trying to be cool and local. But the tacos were so amazingly delicious that you can’t hold it against them. Or against Chicago for bringing them in. Feel very grateful for all the Lyft drivers in Chicago as you climb into your ride home. Be even more grateful for the incredibly comfortable hotel mattress. And blackout blinds.
Day Four:
Wake up. Head back to Eataly on your way to the airport because you have no shame and you saw yesterday that they have BREAKFAST PANINIS on their menu. Discover that yes – they really are as good as they sound and you now have zero guilt about eating at the Italian food IKEA, even if GOOP is somehow involved which they probably are given that Mario Battali is behind this place. Gwyneth has good taste – what can you do about that? Ponder this while you walk to the station to take the El to the airport.
Realize that Chicago has two airports and your phone gave you directions to the wrong one. Be grateful that Chicago’s mass transit is fantastic and easily walk one block up to get on the correct line. Make it (barely) and sleep the whole flight home.
Until next time, Chicago!
Fifty-two Daring 