April trip

Question

Hi all I hope you are well. I am visiting Chicago with my partner for the first time 19-28 April and I was hoping for some help with my itinerary. I posted a long message but it got lost so I am going to try and cover it in an easy summary.

Interests

Sport - baseball booked Sunday at wrigley, would love to see basketball

Sights - best photos/views, museums MSI & Field the best?, river cruise CAC best?, any other must sees?

Comedy/theatre - second city or somewhere else? Would love to get in a show while there although options seem limited

Music - main gigs but also recommendedations for jazz/speakeasy clubs

Food - want to try the Chicago must haves and the hidden gems. Will eat almost anything

Other - any day trips recommended? Any big things I am missing

I have been stalking the forums for a few weeks now to get ideas, we are in 30s (well I'm recently 40) and happy with lots of walking and while we can pay for a special experience if it's worthwhile we will be trying to get the best value out of the trip.

I massively appreciate any help you can offer and apologies in advance for the shopping list style of the message. If there is anything else I can do to help you help me please let me know

Answer

It sounds like you’re in for a fantastic trip to Chicago! April is a great time to visit, with spring in full bloom and plenty of things to do. Below, I’ll break down some recommendations for each of your interests to help make the most of your 9-day trip.

Sport

Baseball: You’ve already booked a game at Wrigley, which is a must-see for any baseball fan. Enjoy the historic ballpark! If you're interested in basketball, check if the Chicago Bulls have any home games at the United Center while you’re in town. April is the tail-end of the NBA regular season, so there's a chance for a game.
Other Sports: If you're interested in seeing Chicago sports culture, consider visiting Guaranteed Rate Field for a White Sox game or taking a sports-themed tour of the city.

Sights & Photography

Best Views/Photos: The John Hancock Center (360 Chicago) or the Willis Tower Skydeck offer great views of the city. But for something a bit unique, head to the Lincoln Park Conservatory or Millennium Park for stunning photo ops, including the famous Cloud Gate (The Bean).
Museums: The Field Museum and Museum of Science and Industry are indeed top-tier. If you enjoy art, also try the Art Institute of Chicago, one of the best art museums in the world, with iconic pieces by Grant Wood and Georges Seurat. The Shedd Aquarium is another good option, especially if you're a fan of marine life.
River Cruise: The Chicago Architecture Foundation (CAC) River Cruise is a highly recommended experience for beautiful views of Chicago’s skyline and learning about the city's architectural history.

Comedy/Theatre

The Second City: This is a classic Chicago comedy experience! If you enjoy improv, it’s one of the best spots for shows in the city, offering sketch comedy and hilarious improv performances.
Other Comedy Venues: For something more intimate, check out iO Theater or The Laugh Factory for more great improv and stand-up comedy.
Theatre: If you're interested in Broadway shows, check out the Chicago Theatre or the Goodman Theatre for fantastic performances. The Broadway in Chicago website will show what’s on during your visit.

Music

Live Music Venues: Chicago has a great live music scene. For jazz, check out The Green Mill Cocktail Lounge (a speakeasy-style bar with great jazz music). Buddy Guy’s Legends is another excellent spot for blues music, as Buddy Guy is one of Chicago’s most legendary blues musicians.
Other Music Venues: For a more contemporary music experience, check out the House of Blues or Lincoln Hall, which hosts live bands and performances of various genres.

Food

Must-Try Foods: Chicago is famous for its deep-dish pizza (try Lou Malnati’s or Giordano’s), Chicago-style hot dogs (head to Portillo’s or Gene & Jude’s), and Italian beef sandwiches (try Al’s Beef). Make sure to also grab some classic Chicago popcorn (Caramel and cheese mixed) from Garrett Popcorn Shops.
Hidden Gems: If you're looking for something off the beaten path, consider trying The Purple Pig for Mediterranean-inspired dishes, or Girl & The Goat for an eclectic mix of small plates.

Day Trips

Day Trip to Oak Park: If you enjoy architecture, visit Oak Park to see homes designed by Frank Lloyd Wright, including the Frank Lloyd Wright Home & Studio.
Lake Michigan Beaches: While April can be a bit chilly, if you enjoy the outdoors, head to the Lakefront Trail or visit the Chicago Botanic Garden for a relaxing day trip from the city.

Other Recommendations

Skydeck at Willis Tower: If you haven’t yet, the Skydeck at Willis Tower offers incredible views and the famous glass-floored viewing ledge.
Cultural Exploration: Explore the Chinatown area for great food, shopping, and a touch of Chinese culture in the city.

It sounds like you have a lot of exciting things planned! With a mix of iconic attractions, food, and culture, you’ll have plenty to keep you busy. Enjoy your trip to Chicago!