4th time in Chicago - this weekend - 2 days - advise

Question

Hello Chicagoans! It is me again, this will be my 4th time visiting Chicago for 2 days this coming weekend! Have been in February last time so more or less know what to expect weather wise but still hopeful to make the best out of it.

Solo female traveler that will stay at Club Quarters by the River. On my prior visits I have done the following: Millennium Park, Cloud Gate, Crown Fountain, Buckingham Fountain, Michigan Avenue Bridge, Magnificent Mile, Holy Name Cathedral, Navy Pier riverwalk, Wendella cruise, 360 Chicago Observation Deck, shopping near Michigan/State, walking Golden Coast with its “mansions”, Oak Street Beach, Starbuck reserva, brushed through Chicago Cultural Center twice and watched The Wicked at The James M. Nederlander Theatre, and Chicago musical at CIBC. Did Chicago greeters guide, the classic buildings, loop area.

Looking what to do this time to enrich further my experience:

Thinking to do Skydeck Chicago for a different angle but almost 100% that it will be foggy

Looking at Navy Pier but doesn’t seem having too much happening. Anything of interest there to do?

Was thinking Lakefront Trail, if not windy. Or perhaps not a good idea?

Maybe visit Art Institute?

Maybe will visit Fields Museum? If I do, I plan to spend entire day there as I am very thorough.

Wanted to watch another show, but looked through Chicago Broadway and not a single show? Am I correct?

I feel like I might be missing on some things as I stopped exploring thinking that I know it all which I know that I don’t. I will not feel comfortable venturing out somewhere outside of Mag mile area too far… Unless you advise on some safe and easy drop in/pick up.

Very much appreciate your comments to the above or anything else to add…. What would be other iconic things to experience?

Answer

Hi there! It sounds like you’ve already explored a lot of the classic Chicago highlights during your previous visits. Chicago is a vibrant city with so much to offer, and I can definitely suggest a few unique and iconic experiences to enrich your upcoming visit. Let’s dive into some suggestions to make the most of your 2 days:

1. Skydeck Chicago vs. 360 Chicago: I completely understand the concern about fog, but Skydeck Chicago (on the 103rd floor of the Willis Tower) offers a different kind of thrill with its glass "Ledge" that extends outside the building—perfect for that jaw-dropping photo opportunity if the weather cooperates. You’re right, it can be foggy, but even on cloudy days, the view of the city’s architecture and vast skyline is still impressive. If you’ve done 360 Chicago (John Hancock), it might be worth trying Skydeck for a different perspective. Alternatively, both spots are iconic, so it just depends on which kind of observation deck experience you’re looking for!

2. Navy Pier: While Navy Pier can sometimes feel touristy, it still has a lot to offer. You can check out the Chicago Shakespeare Theater if you're in the mood for a performance, visit the Chicago Children's Museum if you're interested in interactive exhibits, or take a ride on the Centennial Wheel for a great view of the city and lakefront. There are also plenty of restaurants and bars if you want to enjoy a drink or meal with a view. While it’s not always bustling like in the summer, it can be a good spot for a scenic walk and a relaxed afternoon.

3. Lakefront Trail: The Lakefront Trail is always a great choice for walking, running, or biking, and the views of Lake Michigan are breathtaking. However, since you mentioned you're concerned about wind, it’s important to keep in mind that Chicago's lakefront can be chilly and breezy in the fall. If the weather's nice, it’s one of the best ways to experience the city’s coastline and enjoy the skyline views. If it’s too windy or cold, you can always walk along the shoreline near Navy Pier or find a park along the trail, such as Grant Park or Millennium Park, to enjoy the outdoors without committing to the full trail.

4. Art Institute of Chicago: The Art Institute is a must-see for anyone who loves art. It houses one of the best collections in the country, including iconic pieces like Grant Wood’s "American Gothic" and Georges Seurat’s "A Sunday on La Grande Jatte." You’ll want to dedicate a couple of hours here at least, but it’s an immersive and enriching experience. Plus, the museum’s architecture and the sculpture garden outside are great for photos and peaceful walks. It’s definitely worth your time if you haven't already visited.

5. The Field Museum: If you’re planning to spend an entire day there, the Field Museum is a fantastic choice! It’s one of the most comprehensive natural history museums in the world, and you can easily lose yourself in exhibits like Sue, the famous T-Rex, or the Ancient Egypt collection. There’s so much to explore, and it’s an especially great option if you want a slower-paced day immersed in history and science.

6. Broadway Shows: You're correct that there might not be any big Broadway shows this weekend, but don’t overlook Chicago Theatre, which often hosts some amazing performances. Check out the events there, as they might have concerts, comedy shows, or unique local productions that are still worth experiencing.

7. Iconic Experiences You May Have Missed: Since you’ve already visited many major attractions, here are a few more experiences that could enhance your trip:

Architecture River Cruise: If you haven't already, take a Chicago architecture boat tour from the Chicago Riverwalk or from a spot near Navy Pier. These tours offer a fascinating overview of the city’s iconic buildings and its architectural history, and the views from the water are stunning.
Lincoln Park and Lincoln Park Zoo: If you want to stretch your legs and enjoy a bit of nature, consider visiting the Lincoln Park Zoo (free admission) or strolling around Lincoln Park itself. The zoo is one of the oldest in the country, and the park offers lovely paths and lakefront views.
Chicago History Museum: If you’re interested in history, the Chicago History Museum offers fascinating exhibits on the city’s past, including its origins, the Great Chicago Fire, and its role in American history.
Chicago Pedway: Explore Chicago’s underground pedestrian tunnels, which connect buildings and are especially useful in bad weather. It’s a fun, quirky way to explore the city without dealing with the elements, and it gives you a unique perspective of the downtown area.

8. Venturing Outside of Michigan Avenue: While you mentioned staying close to the Mag Mile, if you're comfortable venturing a little further out, you can easily hop on public transport to visit neighborhoods like Wicker Park, Logan Square, or Pilsen, where you can explore local art scenes, murals, hip cafes, and unique boutiques. These neighborhoods are safe and easily accessible, and they offer a local vibe that's a bit different from the tourist areas.

9. Food and Drink: Since you love exploring, don’t miss out on Chicago’s amazing food scene. Try some local specialties:

Deep-dish pizza at places like Lou Malnati’s or Giordano’s.
Chicago-style hot dogs from Portillo’s or The Wieners Circle.
Cocktail bars like The Aviary or The Violet Hour.

Lastly, always check the weather forecast as Chicago can be unpredictable in September. If the weather doesn’t cooperate, consider heading indoors to explore the Museum of Science and Industry or the Adler Planetarium for a more sheltered day.

Chicago is a fantastic city, and no matter what you choose to do, you’re sure to have a great time! Enjoy your trip and feel free to reach out again if you need more ideas!

4th time in Chicago - this weekend - 2 days - advise

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