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Skip the Wingstop and drop into this casual sports bar for the best wings in the city. Since our wedding weekend will overlap with the NBA playoffs, this is a perfect place to sit, socialize, and watch the game.

Tyree’s Recommendation: ½ Lemon Pepper and ½ Spicy BBQ, well done.

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Right off the water, this restaurant offers a nice alternative to the ultra-heavy Chicago-style deep dish pizza (though, if you want deep dish, we recommend Pequods). Watch as Chicagoans pull up on their yachts and order food directly on the dock. There’s a reason the NYTimes has ranked this spot one of the best pizza places in the country multiple years in a row.

Tyree’s Recommendation: Duck Prosciutto Pizza.

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The day after the wedding, you will probably be…. touched…. by the good vibes from the night before. The perfect cure? Chilaquiles from this authentic, homey Mexican spot in Pilsen. Note, the staff doesn’t speak much English, so brush up on your Spanish and be respectful.

Angel’s Recommendation: Chilaquiles Roja with Barbacoa and Over-Easy Eggs.

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This Black-owned breakfast spot may not take reservations, but the wait is always worth it. Known for their french toast flights, this restaurant now has two locations— one in Lincoln Park and a second in South Loop. Both are great options for a casual, homey meal. Make no mistake, the savory options are just as good as the sweet. The kind and humorous staff is just the cherry on top.

Angel’s Recommendation: French Toast Flight and Catfish and Eggs.

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If you are looking for a dining experience that is as fancy as it is cozy, Le Bouchon is the place for you. This traditional French bistro is a favorite of the Bride’s and a Chicago classic. Pro Tip — Go on Monday for half-priced bottles of wine.

Angel’s Recommendation: Fjord Troute en Croute.

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Few restaurants are as consistently good and understated as Giant. This compact Logan Square spot serves modern yet approachable food that is as unique as it is delicious. This would be our top choice for a date-night in Chicago. It is also walkable to a several wonderful cocktail lounges and wine bars.

Angel’s Recommendation: Saffron Tagliatelle and Jalapeño Biscuits

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This southern, Black-owned restaurant is the perfect dinner spot if you want comfort food with a modern edge. Conveniently located in the Loop, this restaurant offers eye-catching appetizers, bold entrees, and a sleeper-hit wine list with an extremely attentive and well-educated sommelier.

Angel‘s Recommendation: Oxtail & Grits and Peach Cornbread Upside Down Cake.

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For 75 years, this casual spot has been supplying Bridgeport with the most indulgent, hearty, nap-inducing breaded steak sandwiches. Some people argue that is is the best sandwich in the world… the Groom doesn’t disagree.

Pro tip — Find an empty table, cozy up next to a construction worker, and eat your sandwich in the restaurant. This isn’t meant to travel.

Tyree’s Recommendation: Regular Size Breaded Steak Sandwich with everything and hot peppers.

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Situated behind a street art and sticker covered door, you will find Sawada. This space shares a venue with a BBQ joint and pumps out some of the best, most reliable coffee in West Loop. Pick up a drink and then stroll around the trendiest neighborhood in Chicago. There, you can people watch, shop, and eat to your heart’s content.

Angel’s Recommendation: Military Latte with Vanilla Syrup and Oat Milk.

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Money doesn’t buy happiness, but it can buy a fruit tea with boba and jelly. At the end of the day, isn’t that kind of the same thing? This Chicago staple has many locations, but the Groom is partial to the location in Chinatown plaza. This plaza is full of unique shops and restaurants, and it regularly has live music and festivals.

Tyree’s Recommendation: Chocolate Lovers Ice Cream Milk Tea and a Bubble Waffle.

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This nondescript juice and smoothie bar is perfect for anyone who wants a healthy and fresh beverage. From freshly pressed juices to vegan protein shakes, this small Latinx owned business is the ideal stop after a workout or long walk. Pro Tip — They also sell tamales out of the back that are shockingly good and generously sized.

Angel’s Recommendation: BYO Smoothie.

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If you want a dark, sexy, understated bar, this is the place for you! The drinks are forward-thinking, global, cross-cultural, experimental, and always delicious.

Angel’s Recommendation: The Greener the Better and French 75 (not on the menu but the girls want what the girls want)

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If you want an impossibly cool, local spot that goes from coffee to cocktails effortlessly— check out this Bucktown gem. The music is a vibe, the drinks are creative and delicious, and the staff is down-to-earth. Pro tip — The owner’s spouse is allergic to nuts, so everything is nut-free!

Angel’s Recommendation: Whatever specialty Gin & Tonic is in season.

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Whether you are beginning your night or wrapping it up, the Hoxton is our go-to place to see and be seen. This lively hotel lobby is large enough that you won’t struggle to get a table but popular enough that the fun never ends. Stop by for a drink (or 3) and enjoy nightlife in Chicago.

Angel’s Recommendation: Glass of Prosecco and a French 75.

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Expat is cozy, sexy day-to-night spot on the edge of West Loop. Sharing a wall with one of the Bride’s favorite restaurants— Coquette— Expat is a reliable choice when you want a comfortable seat, an excellent and balanced cocktail, and house music. The crowd is young, brown, and cool. If you aren’t a frequent flyer, you’re doing it wrong.

Angel’s Recommendation: Pornstar Martini (Frozen) and a side of fries.

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Let’s address the elephant in the room— The Aviary is very pricey. It is the sister establishment to Chicago’s famous 3-Michelin-Star restaurant, Alinea. The drinks are incredible and, more importantly, the non-alcoholic cocktails are some of the best the Groom has ever had. If you do not drink alcohol and want to treat yourself to an evening you won’t soon forget, we couldn’t recommend this place more.

Tyree’s Recommendation: 3-Course N/A Cocktail Progression.

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No trip to Chicago is complete without a trip to the Art Institute (AIC). Considered one of the top museums in the world, the AIC has something for everyone— Impressionism, contemporary art, ancient artifacts, interactive opportunities, and limited exhibits. The sculpture garden is a special treat when the weather is good.

Angel’s Recommendation: Thorne Miniature Rooms.

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This hip, retro bowling alley is the perfect way to spend an afternoon or evening. This spot is 21+ after 7:30 PM, making it the perfect afternoon hang with young ones or evening hang for adults. We also recommend this spot for guests who want to step away from the touristy parts of Chicago and check out a more residential area.

Tyree’s Recommendation: Be prepared to score your own game (boo), but you can also bring in your own outside food which is a plus.

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Do you love architecture, history, and getting some fresh air? If the answer is yes, you will love the Chicago brick tour! This walking tour is run by a solo, passionate man who takes visitors through different neighborhoods and teaches about the history within each brick laid. I guarantee you will see the city in a new light and get your steps in.

Angel’s Recommendation: Bronzeville Walking Tour.

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When the weather is good, nothing is better than an open-air movie. This rooftop theatre plays classic titles that we all know and love. Popcorn is free and the other snacks are shockingly good. The views? Priceless. When the show is over, you will find yourself in the heart of Fulton Market surrounded by some of the best restaurants and bars the city has to offer!

Tyree’s Recommendation: Try to catch a black cinema classic like Love, Jones.

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Though neither the Bride nor Groom grew up in Chicago, Mr. Kite’s somehow makes them feel like children again. This small, old-school chocolate shop is located on the restaurant-heavy street of Division. Once inside, you can choose from the hundreds of chocolates or opt for a classic chocolate covered strawberry, but be prepared to wait while Mr. Kite’s wife dips them in real time.

Tyree’s Recommendation: Cookie Dough Milkshake and a milk chocolate covered pretzel stick.

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It is no secret that the Bride loves to shop vintage and second-hand whenever possible. If you want to experience Chicago’s vintage shopping scene for yourself, check out the Vintage House Market. This is a bi-monthly vintage and handmade market aiming to showcase local Chicago makers. You can find out exactly where the next market will be via the website or Instagram.

Angel’s Recommendation: Expect the unexpected. Also, if second-hand isn’t your thing, there are many new items made by local artisans!

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If you’re not used to suffering for your jazz, this is not the place for you— go to Winter’s Jazz Club in River East or Andy’s Jazz Club in River North instead. If you are a serious listener who wants attuned, contemplative, experimental music and are comfortable standing— run to Green Mill. Then again, you’ve probably already heard of it.

Angel’s Recommendation: Beer. The cocktails suck. Also, bring cash. They don’t take card.

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The Bloomingdale Trail, also known as the 606, is a 5-mile-long raised walking trail that runs through the northwest neighborhoods of Chicago. The Bride and Groom live off the 606 and can be found there nearly every evening walking their dog, Honey Bun. The 606 is the perfect place to walk, run, or ride your bike. There are coffee shops, restaurants, bars, parks, and other interesting things at each entrance. However, the best perk is the birds-eye view into some of the most beautiful homes in the city.

Tyree’s Recommendation: If you are an advanced or experienced skater, this is a great spot— very smooth, with nice slopes to catch some speed.