On a recent trip to Chicago, we had the benefit of traveling with someone who previously lived there for many years. We didn’t get to visit all her favorite haunts, but it was helpful to have someone curate options from the overwhelming array of restaurants in this food-rich city. Our eclectic tastes took us to spots fit for everyone from the frugal to the foodie. In case you don’t have your own personal culinary tour guide, here’s a sampling of 5 Chicago food groups (and two bonus buys) for your time in the Windy City:
1. Deep-dish delicacy
No trip to Chicago is complete without their famous deep-dish pizza, so that was our first order of business. Based on proximity and reputation, we landed on Giordano’s but there are countless wonderful pizza spots and locals will happily share their favorites, so just ask around (most people I asked quickly named 2-3 they love).
Remember they call these pies for a reason and adjust for the fact that each slice is as thick as a wedge of my aunt’s best pies piled with skyscraping meringue. We made a rookie move by over-ordering but that gave us a chance to try several kinds and take enough back to our hotel kitchen to enjoy for a midday meal later in our stay.
After tasting three different flavors, I definitely agreed with our former resident and guide that the fresh spinach and cheese pizza was the best. The guys in our crew favored the “Meat and More Meat” and Chicago Classic (pepperoni, mushroom, green pepper and onion).
While we waited for our pizza, I tasted their deep-fried cheese curds on their “limited time offer” appetizer menu. As a Wisconsin native, I know my way around this snack and found Giordano’s to be some of the best I’ve ever had, no doubt thanks to the use of Wisconsin white cheddar curds! I hope they keep these around until you can come try them.
2. Chicago dogs
Even if you normally don’t go for the hot dog scene, Chicago dogs take it to another level. The typical Chicago dog is an all-beef hot dog on a poppy seed bun piled with peppers, pickles, onion and more.
We hoped to get to Portillo’s for our fix, but ended up at Wrigley Field for a Cubs game on National Hot Dog Day, so we moved our hot dog slot up a few days.
At both Wrigley and Portillo’s, another alternative is the Italian beef – I loved the shaved beef on a hoagie but my bun was quickly soaked from how juicy the meat was, so eat fast!
3. Neighborhood nosh
Don’t be afraid to get off the tourist track. While on the north end of town, we took the train over to a great neighborhood not far from Lincoln Park Zoo that was filled with fantastic restaurants like Café Ba-ba-Reeba (I definitely want to hit this chic spot for tapas and sangria next time!) and the Taco Joint.
Failing to plan for the after work and Friday night date crowd, the waits were long everywhere, but our patience paid off at Pasta Palazzo (which claims to be the “cool neighbor” on Halsted Street) when a table opened up after we hovered a while with a cool drink. Smaller parties were able to get in even faster thanks to a few seats around a counter bar area, which also had a bird’s eye view of the authentic pasta dishes getting plated next to the fresh asparagus being grilled to perfection.
My house-made ravioli with pomodoro sauce wasn’t the only dish getting rave reviews and a cleaned plate. The grilled salmon special was impressive and the homemade gnocchi is still bringing back happy memories of a relaxed but lively meal served by friendly staff at reasonable prices. Check out their fun menu that also offers takeout and delivery.
4. Futuristic food court
After a hot day at the beach, everyone was hungry but they all seemed to be in the mood for something a little different. We were fresh off the sand and in search of a casual setting in comforting air conditioning.
That’s when Water Tower Place came to the rescue. Inside a shopping center just a short walk from Oak Street Beach on our way back to the Miracle Mile, we stepped inside a bazaar of restaurants enclosed in an updated concept of a food court.
We stated our party size at the entrance to Foodlife and waited briefly to be shown to a large table cleaned and ready for our big group. Each person from kid to adult was given their own plastic card to swipe at whatever station they chose for their meal and then the tab could be consolidated by the adult paying as we exited. Check out the short video showing how it works and some of the delicious choices.
The street tacos at their Taqueria were some of my favorite food choices on the trip – a little collection of flavor ranging from chicken tikka to steak and topped with my tailored choices of sauces, onion and cilantro. Others in the group preferred dumplings and rice dishes from Chinese and Japanese food stations. If I wasn’t surrounded by some of the best barbecue restaurants back home, I might have been tempted by the impressive pulled pork and soul food side dishes that I saw one patron taking back to her table.
5. Big City Diner
On our last day, we were in search of a more portable option that could be ordered and taken on the road. Fate brought our footsteps to the Eleven City Diner, bursting at the seams with old-fashioned treats, diner food and deli sandwiches of the best big city variety. We were taking our orders to-go, but many were enjoying two levels of seating inside. The kids were wowed by their malts and shakes. I tried the “Schwartzy” which lives up to the claim as a “sandwich you’ll never forget” — a juicy brisket sandwich on challah that also comes with au jus to satisfy those French dippers out there. From lox and bagels to burgers and fries, the food there was fresh, satisfying and tasty. They had candy from long ago and drinks you may or may not be reminiscing about. Vernon’s ginger and Dr. Brown’s cream soda – yes, but celery soda?! I’ll leave that one for someone else to taste test.
Two Bonus Buys: Our Favorite Sweet Treats!
Scooped Cookie Dough Bar at Water Tower Place was my favorite splurge of the trip. We saw a dairy farm’s stock of butter being delivered to this decadent dessert stop, so we knew it would be good. The hands-down favorite for the adults was the Cowboy Cookie, while the peanut butter disappointed. Most of the kid crew voted for straight-up Chocolate Chip. Hard to go wrong with that comfort food! They have some standards like Oatmeal Raisin and Monster, along with a few rotating offerings. Here’s the full menu to get your mouth watering. For only a dollar or two extra you can try a few different flavors, making it a great treat for two to share. There’s even milk on tap at the end of the line!
Many know about Navy Pier and their fun carnival rides on the waterfront, but inside the marketplace of food and drink shops, you can satisfy your sweet tooth in every possible way. The Chicago classic, Garrett’s Popcorn, is a local favorite, mixing caramel and cheese popcorn in the city’s famous blend. We got a great tip from our car share driver (a day too late to help us, but happy to share with you!) on the best caramel cake in town at Brown Sugar Bakery, famed South Side bakers who now share their wares at Navy Pier also. The most unique award goes to the mango bubble tea at Snow Dragon Shavery, served in a giant light bulb container – a souvenir bonus that made the trek home with us and is ready to inspire our own home creations for summer sipping!