My husband surprised me with our very first trip to Chicago, and it did not disappoint. Chi-Town offers the friendliness and cleanliness of Toronto, the excitement and food variety of New York, and a calm, cool, medium-sized city vibe that can only be described to those who have been there. It’s almost as though I feel a part of an elite club now; let’s just say we will definitely be heading back in the not-so-distant future.
There are so many restaurants that we simply didn’t have time to check out, but I thought I would compile a list of the favourite restaurants and “must-see” areas that we did make it to for any first, second or one hundredth-time visitors to the city. Chicago seems to be one of those places that there is always something new and exciting to check out!
My Chicago Recommendations:
- Deep dish pizza from Lou Malnati’s This restaurant turned into a chain for a reason: the team at Lou’s knows what they’re doing. We started with a spring salad and then cut right to the chase with the Chicago-style deep dish pizza. Then, based on our friend Kieran’s recommendation, we picked up two frozen deep dish pizzas on the way to the airport to bring home. Tip: They make each pizza from scratch so make sure to order with the knowledge that the deep dish will take thirty minutes.
- Soho House Chicago– Ian and I stayed at Soho House Chicago and it was the best hotel experience we’ve ever had. As a Toronto Soho member, we were able to book a room for the weekend and were pleasantly surprised with all of the amenities and friendly service we received. The gym (stocked with a boxing ring and top-of-the- line equipment) was stunning, the rooftop restaurant (complete with a pool) was party central, and our room was the perfect mix of vintage meets modern (they even had a hot water bottle and a flat-iron in the room for me, and the Cowshed product spread was endless!). The main floor consists of three restaurants, a Cowshed spa and a Speak Easy, which are all available to the general public, so I would definitely recommend stopping in for high tea or the Chicken Shop goodness.
- The Girl and The Goat-
The most recommended restaurant in the city is owned by Top Chef Stephanie Izard, and the open kitchen and it’s dramatic ambiance is just the beginning of the fun when you head to The Girl and the Goat. We ordered off the ‘goat menu’ as well as the main dinner menu, and our favourite dish was unexpected: the calamari bruschetta (clam baguette, goat milk ricotta, goat bacon and green tomato). The restaurant changes its menu frequently, but if you happen to see it (or something similar!) on the menu, I highly recommend. We also loved the pig face dish… seriously awesome.
Tip: Make sure to make reservations here as soon as they open them for the date you want. I believe they open reservations 6-8 weeks in advance. It’s a hot spot and well worth it!
- The Publican–
The Publican was recommended to us by a few people as well, so I was thrilled we were able to make it there for a brunch. There breaky options are unique, Midwestern and flavourful. Check out our dishes below and above!
- The Art Institute of Chicago– The Art Institute was voted best art museum in the world, which is quite the statement! It IS beautiful though; elegant, clean and offers a great mix of artists. I also loved the fact that you could take a “Ferris Bueller Walking Tour” and visit all the pieces that Ferris, Cameron and Sloane do in the movie.
- The Architectural Boat Tour– The boat tour was an activity that was recommended to us by pretty much every person who has ever been to Chi-Town. We bought our tickets online in advance, since we had a specific day and time in mind and didn’t want to risk the tour being sold out (which we were informed as happened to others). It was a beautiful, sunny, HOT day, and I suggest bringing a hat and some water with you- we were sweating! The boat has a seated area in the cabin as well (it’s also where you can purchase libations), but I loved our view from the top deck. Our guide was extremely knowledgeable on all of the buildings and the tour was a great ninety minutes of learning and seeing the beauty the city has to offer. Why didn’t we do something similar with our waterfront in Toronto?
- The Little Goat– The best brunch of the weekend! The Little Goat is a diner right across the street from The Girl and The Goat and- you guessed it- has the same owner. We had the BEST breakfast here, and there is something on the menu for everyone. I started with a smoked pork and toffee crunch milkshake (don’t knock it til’ you try it… it was out of this world!) and Ian and I ended up with, well, see our descriptions and photos below. Highly recommend The Little Goat- remember to make reservations a few weeks in advance.
- Cloud Gate–
The Bean was fun for us to go to because it’s one of those spots that everyone heads to during their first time to Chicago— it’s like a rite of passage or something. It was especially fun for us to check out because I’m pregnant with our own little bean! We saw all the sites; Millennium Park, the amphitheatre, Michigan Ave/Magnificent Mile, Navy Pier…. and of course stopped for the famous Garrett’s Popcorn for some Chicago Mix on our way back to the hotel.
- Big Star Taco– Big Star Taco is located in a great neighbourhood and has one of those massive patios you can just drink margarita’s on all day. Ian tried a “walking taco” (see pictures below!) and my favourite was definitely the fish.
- Stan’s Donuts– Stan’s isn’t what I would call a typical gourmet donut joint; instead, it’s mass-produced, fresh-baked gloriousness sits in heaps behind the counter. It’s overwhelming to decide what to choose, but Ian and I decided to share the Captain Crunch Bismark (meaning creamed Captain Crunch inside the donut, too!) and were beyond happy.
- The 606– I was so happy we experienced a little jaunt on the 606. Comparable to the Highline in New York, but without the views, the 606 is a safe and clean walkway/fitness trail.
I hope my tips and recommendations help you out on your next journey to Chicago! Big thanks to everyone who sent me recommendations…. your reco’s made our trip that much better! I can’t wait to go back 🙂