Ultimate Chicago Travel Guide: Top Places to Stay, Eat, and Explore
Ahhh, Chicago! The Windy City. You feel it as soon as you arrive—the breeze coming off Lake Michigan and the buzz of the city. I recently visited Chicago for a work trip in April, and I hit many of the must-see attractions, soaked in the local culture, and discovered a few spots I can’t wait to recommend. Whether you’re here for business or pleasure, Chicago has so much to offer, and if you’re lucky enough to visit in March for St. Patrick’s Day, you’ll see the Chicago River dyed green—a sight that’s high on my list for next time!
In this guide, I’ll share where to stay, what to do, and where to eat during your two-day adventure in Chicago!
Where to Stay:
We stayed at the Fairmont Chicago in Millennium Park, and it was fantastic. Centrally located, it’s just a five-minute walk from The Bean and the Riverwalk, which made sightseeing a breeze. If you’re looking for something equally convenient but perhaps with a bit more flair, here are some trendy, affordable hotel options:
- The Blackstone – a historic hotel located on Michigan Avenue with modern amenities and classic charm. It’s prime location makes it perfect for exploring the city, with many attractions just a short walk away.
- The Publishing House Bed and Breakfast – A stylish and cozy boutique B&B located in the West Loop. This spot offers a homey yet modern atmosphere, perfect for a more intimate and unique stay in the city. Ideal for travelers who enjoy a personal touch with great breakfast options.
- The Robey – Located in Wicker Park, this boutique hotel blends modern design with vintage charm, offering rooftop views and an artsy vibe. Perfect for those who love stylish, trendy stays.
- The Hoxton – In the Fulton Market District, The Hoxton has a cool industrial design and a great social atmosphere. They also have a rooftop pool!
- LondonHouse Chicago – A luxurious hotel located right on the Chicago River, offering stunning rooftop views and a blend of historic and modern design. It’s perfect for those seeking elegance and a central location near all the major attractions.
- Sheraton Grand Chicago Riverwalk – Situated right on the Chicago River, this hotel offers stunning waterfront views and is within walking distance of major attractions like Navy Pier and Millennium Park. With modern amenities and a prime location, it’s ideal for both business and leisure travelers looking to explore the city.
Transportation: Use the CTA L trains and buses to get around efficiently. The Chicago CityPASS or a day transit pass can help you save time and money on public transportation.
What to Do During the Day:
Go Sightseeing:
The best way to experience Chicago is on foot. I covered so much ground just walking around, and I highly recommend it if you can! Here are some highlights:
- Navy Pier
The iconic Navy Pier is a must-see, especially in the summer when you can take in the beautiful views of Lake Michigan. Take a spin on the Ferris wheel for a panoramic view of the skyline, or simply stroll along the pier to soak up the atmosphere. - The Riverwalk
This stretch along the Chicago River is one of the most scenic ways to explore the city. Lined with cafes and unique public art, it’s a great spot for a leisurely walk or even a boat ride. Pro tip: Make sure to check out the stunning mix of old and modern architecture.
- The Bean (Cloud Gate)
Yes, it’s touristy, but it’s iconic! While under construction during my visit, I still managed to get a great photo with the famous mirrored sculpture. A must for first-time visitors!
- Tribune Tower
Located on Michigan Avenue, the Tribune Tower is one of Chicago’s most historic and striking buildings. Originally the headquarters of the Chicago Tribune, this neo-Gothic skyscraper was completed in 1925 and features fragments of famous structures from around the world, such as the Great Wall of China and the Parthenon in Greece, embedded in its exterior. Even if you’re not a history buff, it’s worth a visit just to see the remarkable architecture and touch pieces of world history. The Chicago Tribune itself, founded in 1847, is one of the city’s oldest and most respected newspapers, and the building remains an enduring symbol of Chicago’s role in journalism and media.
- When in season, catch a Chicago Cubs game at Wrigley Field. As one of the oldest ballparks in the country, Wrigley is a must-see for sports fans. Even if you’re not a huge baseball enthusiast, the atmosphere is electric, and it’s a great way to experience Chicago’s vibrant sports culture.
Book an Architecture Tour:
Chicago is famous for its architecture, and a river cruise is one of the best ways to take it all in.
- Wendella’s Architectural River Tour is Chicago’s original architecture tour, offering a 90-minute and 45-minute tour on the Chicago River.
- Chicago Architecture Foundation Center River Cruise offers a well-reviewed tour that gives you the full history of the city’s skyscrapers and unique designs.
Visit Museums:
Chicago is home to some world-class museums, so if you’re into culture, here are a few worth checking out:
- The Art Institute of Chicago – One of the oldest and largest art museums in the U.S. Don’t miss the impressionist and modern art galleries.
- The Field Museum – A natural history museum housing “Sue,” the largest and most complete T. rex ever found.
- The Museum of Contemporary Art – For lovers of modern and contemporary art.
What to Do at Night:
- Catch a Show at The Second City
Chicago is the birthplace of improvisational comedy, and The Second City is one of the most famous comedy clubs in the world. Comedians like Steve Carell, Tina Fey, and Bill Murray got their start here. I caught “You’ve Got Gamed” during my visit, and it was the perfect way to unwind after a busy workday.
- Book a River Cruise
A river cruise is a magical way to see Chicago at night. Whether you’re in the mood for a historical tour or a lively cocktail cruise, seeing the city skyline illuminated along the water is breathtaking.
Where to Eat:
🍕 Deep Dish Pizza:
- Giordano’s – No trip to Chicago is complete without trying its famous deep-dish pizza. If you want to go full Chicago, get it with all the classic toppings: bell peppers, onions, cheese, and pepperoni.
- Lou Malnati’s – Another spot for classic deep-dish pizza, known for its buttery crust. It’s a local favorite, so you know it’s the real deal.
🍽 Dining:
- Girl & the Goat – One of Chicago’s most popular and critically acclaimed restaurants, offering inventive, globally inspired small plates. Located in the West Loop, it has a lively atmosphere and a fantastic selection of unique dishes, making it a must-visit for foodies. I heard from a friend that you must try the roasted pig face, even if you are a picky eater.
- Lyra – A trendy spot with Mediterranean-inspired cuisine, great cocktails, and a chic atmosphere. Perfect for a night out if you’re looking for good vibes and delicious drinks.
- Frasca Pizzeria and Wine Bar – Cozy and welcoming, this spot in Lakeview is known for its wood-fired pizzas and extensive wine selection. A great place to unwind with friends after a long day of sightseeing.
- La Scarola – A charming, old-school Italian restaurant offering hearty classics. The cozy, intimate setting makes it a great spot for a comforting meal.
- Utopian Tailgate – A fun, rooftop bar with vibrant décor and an energetic atmosphere. It’s ideal for grabbing drinks with friends while enjoying a view of the Chicago skyline.
🍿🌭 Snacks:
- Garrett Popcorn – Don’t leave Chicago without grabbing a bag of Garrett’s famous popcorn. The mix of caramel and cheddar cheese popcorn is strangely addictive and makes the perfect snack for your flight home!
- Portillo’s – For an authentic Chicago-style hot dog (no ketchup!) or an Italian beef sandwich. A must-try for any foodie visiting the city.
What to Pack:
- Comfy Shoes – You’ll be doing tons of walking, so make sure to pack supportive footwear. Trust me, your feet will thank you!
- Windbreaker/Rain Jacket – Chicago weather can be unpredictable, and the wind is no joke. Be prepared with a light, packable jacket in case it rains or gets breezy.
- Hair Tie – If you’ve got long hair, you’ll definitely want to keep it tied up when you’re out exploring. The wind will not be kind to your hairstyle!
- Portable Charger – A lifesaver when you’re constantly on the go. Keep your phone charged so you can snap all the pics and navigate the city without worry.
🎵 Chicago Tunes to Spark Inspo for Your Trip 🤍:
- “Chicago” by Michael Jackson
- “Chicago Freestyle” by Drake
- “You’re the Inspiration” by Chicago
- “End of Beginning” by Djo
- “Chicago” by Sufjan Stevens
Final Thoughts:
Chicago is a vibrant city with something for everyone. Whether you’re there for business, sightseeing, or eating your way through town, two days is just enough to get a taste of what the Windy City has to offer. Can’t wait to go back—hopefully in the fall or for that infamous St. Patrick’s Day river dye!
