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One Flight Away: A long weekend guide to experiencing and tasting Chicago

One Flight Away: A long weekend guide to experiencing and tasting Chicago

View of the Chicago skyline from Nobu Hotel
View of the Chicago skyline from Nobu Hotel

Chicago is always a good choice for a quick getaway from Tampa. Probably not the first choice for winter, but, spring and summer in the Windy City is a no-brainer.


With non-stop flights from Tampa International Airport on a daily basis, it is one of our favorite cities to visit for a quick weekend getaway. Like some of you, to extend our stay in Chicago, we left on a holiday that is July 4th.

Where to stay. We tried a couple of options on our most recent travels to Chicago. 


The Nobu Hotel in the West Loop was the ideal spot with its own highly-acclaimed Nobu Restaurant and surrounded by restaurants and bars all over. Besides the well appointed rooms and suites, the hotel boasted of amenities that makes for a next level experience. It had a nicely equipped fitness gym with sauna and a pool and a rooftop bar with stunning views of the Chicago skyline. The rooms are sleek and modern yet minimalist.

If you’re staying for an extended period but want hotel-like amenities, Kasa is a unique option. Located in the River North area, these long and short term units come with a kitchen so you don’t have to worry about eating out every night if you’re staying a while. The building has a rooftop pool, lots of stylish common areas for work from home/digital nomad types and two gyms with extensive equipment.

At first it may seem a bit dorm-like, but the amenities and easy access grew on me. It’s also a bit less trendy and crowded than the West Loop area yet near the train, plenty of dining options and a Whole Foods just a few blocks away.

Now, let’s get to the meat. But first, we need caffeine.

Sawada Coffee is probably the best coffee shop you’ll find in the entire city of Chicago. Don’t believe us? Just check their Google ratings. They serve the best cappuccino and cortado in our opinion. Best to get there as soon as they open as the lines in the morning get fairly long if you’re in a rush.

Here are some of the best eats in levels of affordability that we discovered and recommend in our quick jaunt to the big foodie city.


In the mood for summer margaritas? Our local friend, took us to Tuco and Blondie for all the margarita fruit flavors you can possibly think of, freshly squeezed. Pair those cocktails withnachos and guac and you’re set! Hungry for more, the deal is in the taco platters with three tacos of your choice protein served with rice and beans. Now you can keep drinking those margs. 😉

Tuco and Blondie
3358 N. Southport Ave.

What would an article about Chicago be without at least one visit to an Irish Pub. O’Leary’s Public House is a great spot to grab a stiff cocktail or a beer and if you’re a bit peckish, we’d recommend the chicken tenders. Great location to view the skyline and people watch without feeling rushed and quite affordable. 

O’Leary’s Public House
541 N Wells

Want a slice of pizza because you’re in Chicago? We tried Giordano’s because it’s been heralded as the classic spot to visit for a deep dish. Based on our experience, we’d say it’s overrated. The wait for service and before, during and after eating was so sloooooow that by the time the pizza got delivered, your quick lunch has turned into an episode of Real Housewives reunion. (Cue Teresa Giudice flipping table gif).


With the highly rated and awarded modern Japanese restaurant, Momotaro, fully booked, it was easier to find a spot for four at its basement level called The Izakaya. With a more Japanese street-style vibe serving shared plates at more affordable prices, it was a gem of a find. 

Get the gyoza with pork and chicken filling. We liked it so much we ordered it twice. The chicken katsu is nicely breaded with the meat cooked perfectly. Lastly, the chahan which is a bowl of beef fried rice with mushrooms and a poached egg is one of the best things on the menu. 

Izakaya at Momotaro
820 W. Lake Street

Split photo of the entrance door and graffitied wall of Gaijin and a close up of an okonomiyaki
Go to Gaijin for the okonomiyaki

This trendy hotspot will transport you straight to the streets of Japan with its mouthwatering okonomiyaki. Gaijin’s take on this savory pancake is packed with umami flavors and an irresistible combination of toppings.  The cozy ambiance and friendly staff add to the delightful dining experience. Whether you’re a seasoned fan of Japanese cuisine or a curious foodie looking to try something new, Gaijin’s okonomiyaki is a must-try culinary adventure.

950 W. Lake Street

Get ready for a finger-licking barbecue experience at The Publican in Chicago! Their tender, smoky brisket and succulent ribs are legendary. Creamy macaroni and cheese, tangy coleslaw, and crispy hush puppies are just a few of the mouthwatering options that perfectly complement their barbecue delights. A must-try culinary adventure that’ll leave you craving more!

The Publican
837 W. Fulton Market

One of the best ways to get a breathtaking view of Chicago is actually at the Signature Room on the 95th floor of the Hancock Tower where you can get a cocktail at the same time. The room could probably use an update but if you just wish to get a few snaps and selfies with the view, it should do the trick!

The Signature Room & Lounge
875 N. Michigan Ave.

The bar at Apolonia with recessed shelves full of liquor
The bar at Apolonia

You an embark on an enchanting culinary journey that’s a little off the beaten path at Apolonia in Chicago. Their reasonably priced tasting menu is a symphony of flavors, artfully presented with locally sourced ingredients. Immerse yourself in an unforgettable dining experience, leaving you yearning for more. It was probably our favorite discovery on this last visit. Apolonia has been recognized with a Michelin Bib Gourmand accolade.

2201 S. Michigan Ave.

Seoul Tacos exterior with sign and outdoor seating

Seoul Taco fuses traditional Mexican style street food with Korean flavors and spices. The Munchwrap Seoupreme is crunchy and soft with your choice of protein (including tofu) and mixes the traditional refried beans and cheddar cheese with kimchi and gochujang sour cream. A selection of three tacos with your choice of protein will only run you around $10 and were plenty filling.

Seoul Taco
738 N Clark St.


Building brick facade of Perilla restaurant in Chicago
Don’t miss to check out the outdoor deck at the back of Perilla in Chicago

Our first dinner as soon as we landed in Chicago did not disappoint. Perilla, a Michelin Bib Gourmand recipient, serves a modern Korean-American menu in its casual yet cozy joint. Our favorites included the Korean pancakes, pork dumplings and marinated Japanese wagyu grilled hibachi-style! Pro-tip: come early before your reservation and grab a cocktail with your friends at the back bar and chill before dinner in their outdoor space with plenty of seating.

401 N. Milwaukee Ave. 

Close up of the Tlyuda Cecina. A plate of corn tortilla covered in guacamole, chorizo, cecina, black beans and spices
Tlyuda Cecina at Tzuco is a must order!

Brunch at Tzuco is highly recommended. This hidden gem by Michelin-starred Chef Carlos Gaytan in Chicago’s Gold Coast will sweep you off your feet with its tantalizing flavors and warm ambiance. Picture this: you step into Tzuco, greeted by a welcoming atmosphere that instantly sets the tone for a delightful culinary adventure. Our favorites on the menu included the Lobster Taco and the Carne Asada Huarache. But you better order the Tlayuda Cecina which was a burst of spicy Mexican flavors over a large plate of crispy tortilla!

720 N. State St.

For lunch and/or fast casual, I have two really great recommendations. First, True Food Kitchen (TFK) is another highly rated restaurant known for high quality food ingredients and is self-described as the “only restaurant fundamentally based on science which ensures all of its craveable dishes and drinks work to increase the longevity of our people and planet.” The Bison Sausage Pizza has organic DiNapoli tomato sauce, charred scallion salsa verde, mozzarella, cotija, jalapeño and was phenomenal. While I was worried it would be too much for one person, I devoured it with no issues. The carb load was perfect for the nearly four miles I walked around the city that day. 

1 W Erie St.

Located near our Kasa stay, The Franklin Room is a highly rated eatery which also boasts an impressive list of whiskeys, bourbons and ryes. I opted for a martini made with vodka from a Chicago-based distillery. Being solo, I couldn’t book a table so was able to get a seat at the bar. Having had a late lunch, I wasn’t super hungry so opted for two smaller items. The lamb chops with chimichurri, coconut milk and parsley were delicious and cooked at the perfect temperature and the kale and roots salad was healthy and light, yet very tasty. 

The Franklin Room
675 N. Franklin


Now, if you’re really in the mood for a culinary experience and a splurge, consider George Trois. Winner of Restaurant of the Year in 2019, we snagged a couple of the 20-seat, 8-course tasting menu at the highly acclaimed French restaurant on the edge of Chicago. The bite in every single course was tres magnifique with innovative presentation and flavors we’ve never tasted before. Just make sure you’ve carved out the time for this ceremony…and the drive if you are staying closer to downtown Chitown.

George Trois Restaurant
64 Green Bay Rd., Winnetka


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