travel: chicago. the food, fun & skyline views.
My 5-Day Itinerary Full of Food, Fun & Skyline Views:
Last year, I shared my first Chicago adventure (you can read that post here), and I couldn’t wait to return. This time, I had five full days to dive deeper into the city’s landmarks, food, and hidden gems. From SkyDeck thrills to concerts, architecture tours, and Wrigley Field, here’s how it all unfolded.
Day One: SkyDeck Chicago & Starbucks Reserve Roastery
I landed bright and early (7:20 a.m.) and headed straight into the city. After dropping our bags at the hotel, we went to SkyDeck Chicago. Standing on The Ledge is just as thrilling as the first time—it’s a must for anyone searching for the best Chicago skyline views.
Next up: caffeine! Chicago’s Starbucks Reserve Roastery is an architectural marvel and a coffee lover’s dream. Mid-afternoon, we hopped on the Chicago Architecture River Cruise, one of the top things to do in Chicago. Learning the history behind the skyline made me fall in love with the city all over again.
After some downtime at the hotel, we had dinner at The Dearborn, a favorite from my first trip. Dining with my friend Andrea, who got us reservations, was the perfect way to kick off our return to Chicago.
Ally’s Mini Chicago Travel Guide: Tips & Must-Dos
1. SkyDeck Chicago
Best time to visit: Early morning to avoid crowds and get perfect skyline photos.
Tip: Don’t miss The Ledge—it’s scary but worth it for the views.
Nearby: Grab coffee at the Starbucks Reserve Roastery afterward.
2. Starbucks Reserve Roastery
Best drink: Seasonal latte or any fun espresso cocktail.
Tip: It’s five stories tall—take time to explore each floor.
3. Architecture Cruise
Best time to book: Afternoon for sunset cityscape shots.
Tip: Bring sunglasses; the river can be reflective mid-day.
4. Art Institute of Chicago
Must-see pieces: Monet, Warhol, and iconic Chicago-focused exhibits.
Tip: Arrive early to avoid crowds and enjoy quieter galleries.
5. Navy Pier & Fireworks
Best time to visit: Evening during fireworks (usually summer weekends).
Tip: Grab snacks and find a lakeside spot for photos with the skyline.
6. Wrigley Field & Wrigleyville
Tour tip: Wear comfortable shoes; the stadium walk is long but worth it.
Nearby eats: Plenty of casual restaurants and pubs—great for lunch or dinner.
7. Must-Try Chicago Foods
Deep-dish pizza (Lou Malnati’s or Giordano’s)
Chicago-style hot dogs
Garrett Popcorn (mix of caramel & cheese!)
8. Photo Ops & Hidden Gems
Cloud Gate (The Bean)
Buckingham Fountain
Any skyline view from rooftops or SkyDeck
Random street art in downtown Chicago
Day Two: Art Institute, Cloud Gate & Buckingham Fountain
Friday was a mix of culture and city landmarks. The Art Institute of Chicago is one of my happy places, with masterpieces by Monet, Warhol, and more. Afterwards, we snapped photos at Cloud Gate (The Bean) and enjoyed the serene surroundings of Buckingham Fountain.
We left room in the afternoon for spontaneous exploring: [insert adventure here, e.g., wandering a new neighborhood, checking out a café, or discovering a hidden shop].
Dinner that evening was equally flexible: [insert restaurant or dining spot here].
Day Three: Chicago Theatre & Navy Pier Fireworks
Saturday was all about experiences. We started with the Chicago Theatre Tour, stepping inside one of the city’s most iconic venues. The architecture alone makes this a must-see.
After the tour, we explored Navy Pier—snacks, shopping, and lakeside people-watching included. The afternoon had free space for additional fun: [insert spontaneous activity here].
We ended the night with the Navy Pier fireworks show, an unforgettable experience against the backdrop of the Chicago skyline.
Day Four: Arcade Fun & Seeing More Friends
Sunday began with a lighthearted stop at a local arcade (shoutout to Armand for planning that). Sometimes, the best parts of a trip are just having fun and letting the city guide you.
The afternoon left room for another adventure: [insert spontaneous activity here].
Then I got to see my girl Itzy!
Day Five: Wrigley Field & Gilt Bar
Monday started with a visit to Wrigley Field, a historic stadium in the heart of Chicago. Even if you’re not a baseball fan, the energy and history are unmatched.
Lunch in Wrigleyville gave us plenty of options—from casual bites to cozy pubs. The afternoon had one last open adventure: [insert final spontaneous activity here].
To cap the trip, we had dinner at Gilt Bar. Dark wood, warm lighting, and strong drinks—perfect for a final night in the city.
Day Six: Goodbye, Chicago
Checkout, savor one last coffee, and then head back to the airport. Five unforgettable days filled with Chicago’s magic, rich history, delicious food, and endless fun—it’s always a bittersweet feeling to leave this incredible city behind.
Final Thoughts
This trip was the perfect blend of revisiting beloved favorites and uncovering exciting new gems. From exploring iconic landmarks and world-class museums to enjoying the vibrant atmosphere of Wrigley Field, the lively Navy Pier, and unforgettable concerts, Chicago truly offers something special for every type of traveler.
If you missed my first trip, be sure to check out the original blog post here—it features everything from delicious deep-dish pizza and fascinating art to the iconic Navy Pier experience.
Chicago, you’ve stolen my heart… again.
Last year, I shared my first Chicago adventure (you can read that post here), and I couldn’t wait to return. This time, I had five full days to dive deeper into the city’s landmarks, food, and hidden gems. From SkyDeck thrills to concerts, architecture tours, and Wrigley Field, here’s how it all unfolded.