Chicago Itinerary
CHICAGO
JULY 29 – AUGUST 1
⚾
📍 Airbnb: 1140 West Wilson Avenue 🚇 Transit: Wilson Train Station (steps away)
DAY 1
Wednesday, July 29
1:30 PM
Arrive Land in Chicago! Catch a 35-minute Uber directly to the Airbnb.
Head to the Game
Airbnb & Transit Drop off bags and get ready for game night! Then, stop at Michoacán & Deli Spot Shop on the walk to Wilson Station. Take the Red Line south to Rate Field (~45–60 mins travel time).
Nearby Eats
Dinner & Drinks near the Park Ballpark Pub (casual beers, burgers, and patio) or Cork & Kerry at the Park (traditional Irish beer garden).
6:40 PM
Yankees vs White Sox ⚾
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CHICAGO
JULY 29 – AUGUST 1
⚾
DAY 2
Thursday, July 30
By 9:30 AM
Emerald City Coffee Walk over for fresh breakfast and coffee to power up the day.
10:00–10:30 AM
Bike Ride along the Lake 🚲 Rent bikes via the Divvy app. Take the Wilson Lakefront Trail south. Stops: North Avenue Beach, Oak Street Beach, Navy Pier (quick pass, not long stay), and end near the Riverwalk.
1:35 PM
Architecture River Tour 🚢 Meeting point: 400 N Michigan Ave. Arrive 30 minutes before departure. Add $90 to Splitwise for Brian.
After Tour
Lunch & Exploration Grab legendary deep dish pizza at Pizzeria Due. Next, see The Bean and head to LondonHouse Bar (hotel rooftop with sweeping views).
Dinner & Bars
Old Town / Lincoln Park Crawl Explore on the bike ride back north: Chicago Pizza & Oven Grinder (pot pies), The Wiener's Circle (Chicago char-grilled hotdogs), Benchmark (sports bar, Happy Hour 5-7pm half priced apps), or Utopian Tailgate (post-dinner rooftop with games).
Late Night
Green Mill Jazz Bar 🎷 Enjoy live swing music with Alan Gresik's Swing Orchestra starting at 8:00 PM at this legendary historical speakeasy lounge ($10 cash cover).
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CHICAGO
JULY 29 – AUGUST 1
⚾
DAY 3
Friday, July 31
Morning
Nabala Cafe Walk to Nabala Cafe for coffee and breakfast. Ride the Red Line south from Wilson Station (only 2 stops to Wrigleyville).
Pre-Game
Wrigleyville Bounce around Wrigleyville before the game. Great spots to hit: Happy Camper (fun patio areas) or Old Crow Smokehouse (rooftop BBQ).
1:20 PM
Yankees vs Cubs at Wrigley Field ⚾ Enjoy classic afternoon baseball at historic Wrigley Field.
Post-Game
Wrigleyville Keep the energy going right after the game at Sluggers (batting cages, skeeball, games, and dueling pianos upstairs on the second level!).
Evening
Head back to Uptown Return back near the Airbnb. Take an optional scenic sunset walk to the lake at Montrose Beach.
Dinner
Dinner Options near the Airbnb: Spacca Napoli Pizzeria (authentic Neapolitan), Fat Cat (comfort food/pool), Agami (sushi vibes), Lucy's Fried Chicken & Smashburgers, or In-On Thai.
Nightlife
Uptown Bars Carol's Pub (honky-tonk), O'Shaughnessy's (Irish pub), Fat Cat (relaxed pool table vibes), Uptown Taproom (sports), or Driftwood (cocktail tavern).
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CHICAGO
JULY 29 – AUGUST 1
⚾
DAY 4
Saturday, August 1
Early Morning
Golden House Restaurant Walk to Golden House for a cozy traditional diner pancake breakfast.
10:45–11:00 AM
Airport Bound (Flight at 2:20 PM)
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