Chicago
Architecture and deep-dish delights
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Plan Your Trip
Chicago Travel Tools
Interactive tools to help you plan the perfect Chicago trip.
Writing Inspiration
Chicago Journal Prompts
Thoughtful questions to capture the essence of your Chicago experience.
Location-Specific
Describe your first view of the Chicago skyline—from the lake, the highway, or the L train.
What was it like to stand beneath the Cloud Gate (the Bean)? What did you see in the reflection?
How did the L train affect your experience—the noise, the views, the neighborhoods it connects?
Describe walking the Magnificent Mile or exploring a neighborhood like Wicker Park or Pilsen.
Sensory Details
Write about the Chicago wind. Did it live up to its reputation?
What was your experience with Chicago architecture—the river cruise, looking up, the mix of old and new?
What was the food scene like? Deep dish, hot dogs, Italian beef—which one won your heart?
Memory Triggers
If you could take one Chicago experience home, what would it be?
What sound will you associate with Chicago forever? The L? The wind? Sports fans?
Describe your most "only in Chicago" moment.
What would you tell someone who thinks Chicago is "just a smaller New York"?
Reflection
How did Chicago's grit and beauty coexist in your experience?
What did the city's history—jazz, blues, architecture, politics—teach you?
If you lived here, which neighborhood would claim you?
What part of Chicago will you carry with you forever?
Photography Guide
Chicago Photo Checklist
Essential shots to capture, with tips from photographers who know the city.
Cloud Gate (The Bean) with skyline reflection
Early morning for empty plaza; get underneath for the omphalos view
Chicago skyline from Navy Pier or North Avenue Beach
Sunset turns the buildings gold against the blue lake
Willis Tower (Sears Tower) from the street
Looking straight up from the base for dramatic scale
Chicago River with bridges and buildings
The architecture boat tour provides unique angles
Buckingham Fountain
Evening for the light show if running (May-October)
Wrigley Field exterior
The ivy and the marquee are iconic even on non-game days
L train rounding a curve in the Loop
The elevated tracks framing downtown are quintessential Chicago
Pilsen murals and street art
The neighborhood is an outdoor gallery of Mexican-American art
Maxwell Street Market vendors
Sunday mornings for the full experience
Jazz or blues club interior
If photos allowed, capture the musicians and the atmosphere
Chicago-style hot dog in action
Never, ever ketchup—the toppings tell the story
Brownstone-lined streets in Lincoln Park
The residential neighborhoods have their own beauty
Places to Remember
Your Chicago Memory Map
Pin these locations in TripMemo and use the prompts to capture meaningful moments.
The Bean Experience
landmark
Cloud Gate in Millennium Park
What did you see in the reflection? How many photos did you take?
Architecture Boat Tour
experience
Learning the city from the river
What building surprised you most? What did you learn?
Your Deep Dish Spot
food
Where you tackled the iconic pizza
Lou Malnati's? Giordano's? Pequod's? How much could you eat?
L Train Moment
experience
Your ride through the city
What did you see from the elevated tracks?
Lakefront Walk or Run
experience
Time spent on Lake Michigan's shore
What was the weather like? How far did you go?
Neighborhood Discovery
hidden gem
The area beyond downtown
Wicker Park? Pilsen? Hyde Park? What drew you there?
Hot Dog Stand
food
Where you got the classic Chicago dog
Did you break the no-ketchup rule? How did it compare to other hot dogs?
Blues or Jazz Club
experience
Live music in the city that invented it
Where did you go? Who was playing? How did it feel?
Sports Experience
local
Cubs, Sox, Bears, Bulls, or Blackhawks
Did you catch a game? What was the crowd like?
Your "Only in Chicago" Moment
personal
When the city revealed itself
What happened that captured Chicago's spirit?
Inspiration
Sample Journal Entries
See how other travelers captured their Chicago experiences.
The Bean at Dawn
Millennium Park, Chicago
Set an alarm for 6am because the internet said it's the only way to see the Bean without a thousand people in your shot. The internet was right. Just me, a jogger, and a security guard who nodded like he'd seen a thousand tourists do this. The sculpture at sunrise is something else: the skyline reflected in curves, the sky turning pink above it, the city still quiet except for the L train rumbling in the distance. I walked around it twice. Stood underneath where everything spirals. Touched the cold metal because everyone does. Some tourist attractions earn the hype.
Photo Captions
- “The Bean before Chicago wakes up.”
- “No crowds. Just reflections and silence.”
- “The skyline curved in stainless steel.”
Deep Dish Surrender
Lou Malnati's, Chicago
Ordered a small. The waiter smiled like he knew something I didn't. Thirty-five minutes later, a cast iron skillet arrived with what can only be described as a pizza-shaped casserole. The crust was buttery and held three pounds of cheese and chunky tomato. I ate two slices and felt defeated in the best way. The table next to me—locals, clearly—finished their whole pie and looked unfazed. I ordered a third slice because I might never be back. Walked it off for two hours along the lake. No regrets.
Photo Captions
- “They said small. This is not small.”
- “The cheese-to-sauce-to-crust ratio defies physics.”
- “Slice two: still confident. Slice three: hubris.”
Ready to write your own Chicago story?
Start Journaling with TripMemoDocument Your Journey
What to Journal in Chicago
Chicago offers countless moments worth capturing. Here are the experiences that make the best travel journal entries.
Architecture
Deep dish pizza
Lake views
Music scene
TripMemo for Chicago
The perfect travel journal companion
- Works offline throughout your trip
- Auto-organize thousands of photos
- See your Chicago journey on a map
- Collaborate with travel companions
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Chicago Travel FAQ
Common Questions About Chicago
What's the best time to visit Chicago?
The best months to visit Chicago are Sep, Feb, Aug when you'll find ideal weather and manageable crowds. Peak season is May, Jun, Jul, while Spring/Autumn offers a good balance of weather and fewer tourists. Climate data sourced from historical weather records.
View data sourceHow much does it cost to visit Chicago per day?
Daily costs in Chicago range from $70 for budget travelers (hostels, street food) to $350 for comfortable travel (4-star hotels, nice restaurants). Budget estimates based on crowdsourced cost data. Use our budget calculator for a detailed breakdown.
View data sourceWhat should I journal about in Chicago?
Chicago offers rich journaling opportunities. Focus on Architecture, Deep dish pizza, Lake views. TripMemo helps you organize photos by location and create beautiful day-by-day entries of your journey.
How do I document a Chicago trip with TripMemo?
TripMemo is perfect for Chicago. Create a TripBook, add photos and notes daily, and watch your journey unfold on an interactive map. The app works offline—essential for areas with spotty WiFi—and organizes thousands of photos automatically by date and location.
Ready to Explore Chicago?
Document your Chicago journey with TripMemo. Create beautiful TripBooks, collaborate with travel companions, and relive your adventure for years to come.