Chicago must-dos?

Question

Am visiting with a friend in October - Thurs 16th - -Sun 19th. After much deliberation we have gone slightly over our hotel budget and booked for the Westin River North (got a very good deal).

Want to see as much of the city as we can and fit in some shopping too, as well as visiting some nice places to eat and drink, maybe see a show too!

I know all this info is available but am really interested in people’s top recommendations for things to do, places to see… You folks on here seem really passionate about your city so am sure you’ll have the best tips!! Thank you

Answer

You're going to love Chicago in October! The weather will be crisp and perfect for exploring the city, and there's so much to do in such a short time. Given that you're staying at the Westin River North, you're in a great spot to get around and enjoy the best of Chicago’s attractions. Here are some must-dos, top places to eat and drink, and recommendations for things you shouldn't miss:

1. Must-See Attractions:

Millennium Park & Cloud Gate ("The Bean"): This is a must-see iconic spot. Walk through Millennium Park, take a picture with the famous Cloud Gate sculpture, and check out the surrounding gardens. It’s also near the Art Institute of Chicago, which is worth a visit if you enjoy art.
Navy Pier: Take a stroll down Navy Pier along the lakefront. It’s a Chicago classic with shops, restaurants, a ferris wheel, and great views of Lake Michigan. You can also take a boat tour from here to explore the city from the water.
Willis Tower Skydeck: Head up to the Skydeck at Willis Tower for breathtaking views of the city. If you're feeling adventurous, try the "Ledge," a glass balcony that extends out from the building for an unobstructed view of the streets below!
Chicago Riverwalk: This is one of Chicago’s newest gems. Take a walk along the river, relax by the water, or enjoy some of the restaurants and bars that line the walk. It’s beautiful in October with the fall colors along the water.
Art Institute of Chicago: A world-renowned museum, perfect for art lovers. It’s close to Millennium Park and has an amazing collection, including Grant Wood’s "American Gothic" and countless Impressionist masterpieces.

2. Shopping & Fashion:

The Magnificent Mile: A must-visit for shopping. This is where you'll find everything from luxury brands to popular department stores. If you're into fashion, this area will be your playground. Don’t miss the historic Water Tower Place for some unique finds as well.
State Street: Another great shopping area that's a bit more down-to-earth than the Magnificent Mile, with department stores like Macy's and boutiques scattered in-between. It’s also home to the Chicago Theatre, so you can check out the marquee if you're nearby.

3. Top Dining and Drinking Spots:

Lou Malnati’s or Giordano’s (Deep Dish Pizza): You can’t come to Chicago without trying deep-dish pizza. Both Lou Malnati’s and Giordano’s are legendary. Lou’s offers a buttery, crispy crust while Giordano’s is known for its cheesy, stuffed crust pizza.
Au Cheval (Best Burger in the US?): This is a local favorite and often regarded as one of the best burgers in the country. If you like burgers, it’s definitely worth the wait. Make sure to try the fried egg on top!
The Aviary: For a more upscale drinking experience, The Aviary in the West Loop offers craft cocktails that are more like works of art. It’s a great spot to get creative and unique cocktails in a luxurious setting.
Gene & Georgetti: Chicago’s oldest steakhouse, located just a short walk from your hotel. Perfect if you're in the mood for a classic, juicy steak and an old-school dining experience.
City Winery: If you enjoy wine, this spot on the river has wine-tasting events, a cozy ambiance, and beautiful views of the river. A great spot for both food and drinks.

4. See a Show:

Chicago Theatre: You can’t miss the grand, historic Chicago Theatre. Check out their schedule to see if there’s a show during your visit. They host everything from concerts to Broadway productions.
Second City: If you’re in the mood for comedy, Second City is the birthplace of many famous comedians (think Tina Fey, Stephen Colbert, etc.). Check out their show for some hilarious improv and sketch comedy.
Chicago Symphony Orchestra: For a more cultured experience, consider attending a performance at the Chicago Symphony Orchestra. They offer various shows throughout the year and are renowned for their incredible musicianship.

5. Other Notable Experiences:

Lincoln Park Zoo: If you want to step outside the city hustle for a bit, head to the Lincoln Park Zoo. It’s free, and the fall season is beautiful in the park with the changing colors of the leaves.
Chicago History Museum: This is a great spot to get to know the rich history of the city, especially if you’re interested in Chicago’s famous history with Prohibition, the 1893 World’s Fair, or the Chicago Fire.
Chicago Architecture Tour: Take a boat tour on the Chicago River to learn about the city’s famous architecture. The views are fantastic and it’s an informative way to see the city’s history and stunning buildings.

6. October Special Events:

Chicago International Film Festival (October): If you love cinema, the Chicago International Film Festival usually takes place in mid-October. You can catch some of the best international and independent films during this time.
Oktoberfest: Chicago loves Oktoberfest! Check out one of the many beer festivals in the city to enjoy craft beer, German food, and live music.

With all of these activities, you’ll be able to enjoy the best of Chicago's architecture, history, food, and culture. October is an ideal time to visit, and you’ll certainly get a great feel for the city in your short stay. Enjoy your trip!