3-Day Itinerary for a Couples Trip to Chicago for a Bulls Game

Explore The Chicago Athletic + Rooftop Cocktails

To make the most of your trip, arrive early afternoon. After you check in to the Chicago Athletic, spend a little time exploring the hotel. It's stunning and there are incredible vintage touches around every corner. Visit the most beautiful basket court you've ever seen downstairs and then head up to Cindy's Rooftop for cocktails with a gorgeous view of Cloud Gate (the iconic bean) and Millenium Park. Trust me, you'll want to take photos here! Even if you don't have a reservation, you can order drinks at the bar and drink them on the patio. If you've got some extra downtime in the afternoon, I recommend ordering a coffee or cocktail and reading a book by the fireplace in the dark & broody lobby lounge.

Dinner + Live Music in River North

Get ready for your first night on the town and Uber up to River North, a trendy young neighborhood filled with food and entertainment. The guys and the gals will both love dinner at Yours Truly, which feels like Carrie Bradshaw herself designed a sports bar. It's not too often you get to enjoy watching a game while sipping on a specialty martini or rare wine. After dinner, walk around the neighborhood and pop into a bar or two for live music. I recommend Blue Chicago for authentic Chicago Blues or Redhead Piano Bar for a more lively option!

Coffee + Art

After a late night of dancing, you'll probably want to sleep in a little bit and you'll definitely need a great latte to kick off your day. Enjoy a brisk morning walk a few blocks from the hotel to Hero Coffee Bar - a hidden gem walkup window between tucked between skyscrapers that feels like you've escaped to Diagon Alley. Enjoy your coffee and breakfast sandwich on the benches by Faces of Chicago.

If you are an art aficionado, you'll enjoy a walk through The Art Institute of Chicago. It's a beautiful museum but small enough to see the highlights in 2-3 hours. If you're not up for the museum tour, there's plenty to see in Millenium Park, including a close up view of The Bean.

Architecture Boat Tour

To see the best views of the City and immerse yourself in the history of Chicago's beautiful architecture, I recommend doing a 90-Minute River Boat Tour. It may sound like a cheesy tourist activity, but believe me, this will be one of the most memorable parts of your trip.

Culinary Adventures in West Loop

While Chicago is probably best known for its Italian food, renowned sushi chefs are taking the City by storm with Omakase. If you're not familiar, Omakase is an intimate Japanese meal where a small group of 6-8 sit in front of the chef as he prepares a tasting menu of his best sushi and ngiri specialites. Omakase isn't cheap, but it's a splurge you will not regret! For dinner tonight, you'll head to Omakase Yume's six seat bar in the West Loop, a foodie centric neighborhood.

Once you're blissed out on mouthwatering fatty tuna, you'll enjoy the half mile walk over to The Aviary. This world renowned cocktail bar is famous for their inventive experiential cocktails. To continue your culinary tour of Chicago, I recommend reserving a table for the 3 Cocktail Progression. Each person in your group will be able to design their own experience and you'll have so much fun as each cocktail is uniquely revealed. You'll want your phones out to remember this special experience!

Brasserie Brunch + Shopping or Self Care

You may wake up counting down the hours to tip off, but you've still got a fun day ahead! Kick off your day with a short walk down to Venteux Brasserie, a French Restaurant that has an attached boulangerie with one of my favorite interiors in the city. It is jaw dropping! If you're feeling like something light, opt for a croissant and cappuccino. If you're up for a full meal, their brunch menu is incredible. Definitely recommend starting off with oysters and french onion soup!

After brunch, you've still got a few hours to explore the city. I would head north up The Magnificent Mile (about a mile walk or a quick uber) to Stadium Goods where you can find some fresh kicks for the game. Right next door, you'll have fun browsing the rare designer duds at The Real Real.

If you prefer a more lowkey day before the excitement of the night, why not treat yourself? Make an appointment at Aire Ancient Baths to soak in ancient Roman, Greek & Ottoman baths or indulge in a massage. You can also send your man to Luxe Barber and Shave Lounge to get an old fashioned shave and a fresh cut.

Game Time

You could get dinner before the game, but I actually think the food options in United Center are pretty great! It's a step up from the usual pretzels and beer. I'd recommend grabbing a snack in The Game Room at the hotel. You can also get in the competitive spirit with bocce, billiards, shuffleboard, and more!

The United Center is just a 10-15 minute Uber from the hotel. You'll want to arrive about 45 minutes before game time so you have time to get in, buy some merch or drinks, and get settled before tip off. You can also watch the teams warm up about 30 minutes before game time.

After the game, you'll probably be ready to crash but if not, you could check out a neighborhood sports bar like Hawkeye's Bar or PB&J (Pizza Beer and Jukebox). I would recommend taking an Uber from the United Center to your next location. It feels safe to walk around in the vicinity of the arena, but the further you get, it's not advised to walk at night.