Our First Trip to Chicago: Things to Visit in Chicago and What to Expect
Steve and I took a quick one-hour flight from Nashville to Chicago for a long weekend in June.
We had talked about visiting the Windy City for years.
Truth be told, big cities aren’t usually our first pick. We usually go for relaxing small towns, scenic mountain drives, or easy beach getaways.
But we finally said, “Let’s do it.” And we’re glad we did.
Chicago surprised us—in a good way.
If you’ve watched the news, you might hesitate. Chicago doesn’t always get the best headlines.
But after hearing from friends and family that it was one of their favorite cities, we had to see for ourselves.
Here’s my honest review of our Chicago getaway—plus helpful travel tips and the best things to visit in Chicago if it’s your first time.
Table of Contents Things to Visit In Chicago
Where We Stayed: Hilton LondonHouse Chicago
We booked a room at the Hilton LondonHouse Chicago, located right downtown along the Chicago River.
The rooms were clean and comfortable, and the hotel’s historic architecture blended beautifully with the city’s skyline.
What do we love most? The location.
It was directly across from the Riverwalk and within walking distance of many top attractions like Millennium Park, The Art Institute, and Michigan Avenue.
The area felt safe, even at night, and I’d recommend it for the location alone.
Travel Tip: The Rooftop Bar Looks Better on Instagram
You’ve probably seen videos of the LondonHouse rooftop bar—the one with jaw-dropping views.
In person, it was much smaller and far more crowded than we expected.
The line to go up was long, and once we got there, it was packed.
While the views were truly incredible, the vibe was too trendy and hectic for us.
If you’re in your 20s or 30s and love that energetic scene, it might be perfect.
But for a more relaxed experience, try arriving right at the opening—11 a.m.
For a few quiet moments, we had the rooftop almost to ourselves before the crowds rolled in.
📍 LondonHouse Chicago (Curio Collection by Hilton)
Address:
85 East Wacker Drive, Chicago, IL 60601, USA
Average Nightly Rate:
– Typical mid-range rate: $249 /night, which is below the Chicago 4‑star average (~$333/night)
– Budget-friendly deals start around $117 /night for standard king rooms:
– Premium suites can go much higher, up to $400+ /night, depending on the season and room type.
What to Do and Things to Visit in Chicago
Listed below are my recommendations for what to do and the best things to visit in Chicago. If this is your first-time guide to the city, these ideas will help you make the most of your trip. From iconic parks to world-class museums, and lakefront views to deep-dish pizza, Chicago offers something for everyone.
If you’re staying near the Chicago River or Navy Pier, purchase a River and Lake Michigan Water Taxi Pass. It’s affordable and makes it easy to visit all the top Chicago attractions without fighting traffic. I’ll link my full post and guide soon.
1. 🚢 Navy Pier
Address: 600 E Grand Ave, Chicago, IL 60611
Admission: Free to enter; parking and activity prices vary.
Navy Pier is one of the most iconic Chicago attractions. It’s home to family-friendly entertainment, shopping, and lakefront dining. While here, try Flyover Chicago, a virtual experience that shows off the city from the sky. Cap it off with a drink at Offshore Rooftop Bar, the world’s largest rooftop bar, with sweeping views of Lake Michigan. This lakefront attraction is easily one of the most popular things to visit in Chicago, with entertainment options for all ages.
2. 🐠 Shedd Aquarium
Address: 1200 S DuSable Lake Shore Dr, Chicago, IL 60605
Admission: ~$39.95 for adults; included with CityPASS.
This world-famous museum of marine life is located near the Field Museum and Millennium Park. It’s home to penguins, sharks, jellyfish, and even beluga whales. A top pick for both kids and adults visiting Chicago for the first time.
3. 🛥️ Architecture Boat Tour
Departs from: Chicago Riverwalk near Michigan Ave
Pricing: ~$45–$60 per person
A favorite among locals and tourists alike. Learn about the city’s famous skyline while cruising through the river. If you’re creating a first time guide to Chicago, this tour deserves a top spot on your list of things to visit in Chicago.
The Boat Tours in Chicago are scenic, relaxing, and one of the best things to visit in Chicago if you want to learn about Chicago’s stunning skyline.
4. 🌳 Grant Park & Buckingham Fountain
Address: 337 E Randolph St, Chicago, IL 60601
Admission: Free
This large public park is often called the “front yard” of the city. The beautiful Buckingham Fountain is a top photo stop and sits just a short walk from Millennium Park and the lakefront.
5. 🫘 Millennium Park and the Bean
Address: 201 E Randolph St, Chicago, IL 60602
Admission: Free
Millennium Park is home to Cloud Gate, better known as The Bean. Cloud Gate is one of the most photographed Chicago attractions. Walk around the gardens, enjoy the public art, and relax in the green spaces just steps from Michigan Avenue.
6. ⚾ Chicago Cubs Game at Wrigley Field
Address: 1060 W Addison St, Chicago, IL 60613
Tickets: Vary by game
Even if you’re not a huge sports fan, visiting Wrigley Field and the Wrigleyville neighborhood is one of the top things to do in Chicago. It’s lively, walkable, and full of fun places to eat and drink.
7. ⚾ Chicago White Sox Game at Guaranteed Rate Field
Address: 333 W 35th St, Chicago, IL 60616
Tip: Uber in and out
The game was enjoyable, but the surrounding area lacks charm. Not a place to wander. Go for the game and then head back to downtown.
8. 🦕 Field Museum
Address: 1400 S DuSable Lake Shore Dr, Chicago, IL 60605
Admission: ~$32 for adults; included with CityPASS
The Field Museum is a must-visit for first-timers. It’s one of the largest natural history museums in the world. Don’t miss Sue the T. Rex, mummies, gemstones, and the cultural exhibits. A cornerstone of the museum campus, this spot blends education and awe.
9. 🌌 Adler Planetarium
Address: 1300 S DuSable Lake Shore Dr, Chicago, IL 60605
Admission: ~$19–$28; included with CityPASS
The planetarium sits on a peninsula with incredible views of the skyline. Step inside for immersive shows about space, time, and the stars. It’s a fantastic add-on after visiting the Shedd or the Field Museum.
10. 🎶 Northerly Island Concerts
Address: 1300 S Lynn White Dr, Chicago, IL 60605
Tickets: Vary by performer – check Live Nation
This outdoor music venue is perched along the lake and gives a truly unique concert experience. Add this to your first-time guide to Chicago if you’re visiting in the summer or early fall. Northerly Island Huntington Bank Pavilion was one of the reasons we visited Chicago this year. We got the chance to see the Dave Matthews Band on our vacation.
11. 🏈 Soldier Field – Chicago Bears
Address: 1410 Museum Campus Dr, Chicago, IL 60605
Best Time: Fall and winter
Catch a Bears game if you’re visiting during football season. This historic stadium is right along Lake Michigan and near several other top Chicago attractions. Steve and I visited Chicago in the Summer, but still made our way over to see the stadium. We will add this activity to our next Chicago Winter vacation.
12. 🚶♀️ Lakefront Trail & Buckingham Fountain
Location: Runs along Lake Michigan
Cost: Free
The Lakefront Trail is a peaceful walking path that connects many of the best things to visit in Chicago—including Navy Pier, Grant Park, and the museum campus. Great for photos, people-watching, and exercise with a view.
The Michigan Lake Trail connects many of the top things to visit in Chicago and gives you a fresh perspective on the skyline.
13. 🎨 Art Institute of Chicago
Address: 111 S Michigan Ave, Chicago, IL 60603
Admission: ~$32; included with CityPASS
One of the most respected museums in the world. See classic works like American Gothic, Nighthawks, and more. Art lovers will be in heaven. It’s also just across the street from Millennium Park, making it easy to bundle both into one afternoon.
14. 🏛️ Chicago Cultural Center
Address: 78 E Washington St, Chicago, IL 60602
Admission: Free
If you love architecture, the Chicago Cultural Center is a hidden treasure. Originally the city’s public library, it now hosts free exhibitions, concerts, and community events. The stained-glass dome is breathtaking.
15. 🍕 Giordano’s Deep Dish Pizza
Closest Location to Riverwalk: 130 E Randolph St, Chicago, IL 60601
Price Range: ~$12–$20 per pizza
Trying authentic Chicago deep dish was at the top of my list of things to do in Chicago—and Giordano’s didn’t disappoint. It’s hearty, cheesy, and truly unique to the city. Make sure to try it at least once!
16. 🍹 Offshore Rooftop Bar
Address: 1000 E Grand Ave, Chicago, IL 60611 (Navy Pier)
Best Time: Sunset!
Located at Navy Pier, this rooftop is perfect for evening cocktails with unbeatable views. The ambiance is lively and upscale. Worth a visit, even just for one drink.
Things We Skipped or Didn’t Love
– Willis Tower Skydeck: Expensive, and crowded, and you can get great views for free elsewhere.
– Smashburger next to LondonHouse: Disappointing food. My milkshake was mostly milk.
– The Chicago Hot Dog at the White Sox game: Didn’t live up to the hype for me, though it’s a bucket-list item for many.
💸 How to Save Money in Chicago
Want to hit all the top Chicago attractions without breaking the bank? Buy a CityPASS before you arrive. It includes entry to the Field Museum, Shedd Aquarium, Adler Planetarium, Art Institute, and more—all at a big discount. It’s perfect for a first-time guide to the city.
Looking for more tips? Don’t miss my full post on Chicago Water Taxi Stops—a budget-friendly way to experience the best things to visit in Chicago from the river and lake.
Final Thoughts on Visiting Chicago
Chicago truly impressed us. There are so many things to do in Chicago that this list only covers the highlights of our summer trip. We packed in as many top attractions as we could, but there are plenty more places we simply ran out of time for.
Keep in mind that this was a summer vacation, so some activities—like lakefront walking paths, rooftop bars, and outdoor concerts—may need to be adjusted if you’re planning a winter visit to Chicago. Many museums and cultural attractions are open year-round, though, and Chicago knows how to embrace the seasons.
Travel Tip: Even with the convenience of the River and Lake Michigan water taxis, you’ll still do a lot of walking. Wear comfortable shoes and light, weather-appropriate clothing. We walked more than we expected, and while it was worth it, my feet earned a rest! On my next trip, I’m adding a spa day to the itinerary—something relaxing to balance all the sightseeing.
If it’s your first time in Chicago, I hope this guide helps you plan an easy, enjoyable trip filled with great food, memorable views, and new favorites.
Check out my full guide on the Chicago Water Taxi Stops to explore the best things to visit in Chicago by boat.
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