Rental Car
Pick Up Your Rental
Pick upMilwaukee · Sep 9
Drop offChicago · Sep 11
Total miles104 mi
Getting There · Step 1
Stay Tonight · Milwaukee, WI
Hotel
Milwaukee Overnight
Check-inWed, Sep 9
Check-outThu, Sep 10
First pitch7:40 PM ET
Book near downtown or the ballpark so your first-game arrival stays simple.
DAY 1
Wednesday, September 9
First pitch at 7:40 PM ET — Milwaukee Brewers vs. Chicago Cubs at American Family Field tonight. Don't leave without Wisconsin Brat (Klement's).
Stop 01 of 02
Milwaukee, WI · Wed Sep 9
American Family Field
Milwaukee Brewers · MLB
7:40 PM ET
vs. Chicago Cubs
Must Eat at the Park
Wisconsin Brat (Klement's)
A Klement's bratwurst grilled over charcoal and served in a hoagie roll with stadium mustard, sauerkraut, and grilled onions.
Local Beer
Spotted Cow
The farmhouse ale sold exclusively in Wisconsin. The most state-exclusive craft beer in MLB.
New Glarus Brewing
The Brewers, Hank the Dog, and Robin Yount
Pilgrim Notes · Milwaukee Baseball History
Stay Tonight · Milwaukee, WI
Milwaukee Overnight
Check-inWed, Sep 9
Check-outThu, Sep 10
First pitch tomorrow at 2:20 PM ET. Leave by 11:02 AM.
Fri Morning
When to Depart
Leave by11:02 AM
Drive to Chicago104 mi · 1.8h
Game time2:20 PM ET
Leave on time to allow for fuel, food, and parking.
Breakfast Stop · Milwaukee, WI
Before You Hit the Road
Diner on the Square
Wauwatosa Square. Proper Midwestern diner breakfast done exactly right. German-influenced egg dishes reflect Milwaukee's heritage. 15 minutes from American Family Field — go before a Brewers day game.
German farmer's breakfast + coffee
Open 7 AM daily
Worth the Detour · +10 min
Gemini Giant Wilmington
A 28-foot spaceman on Route 66 since 1965. The drive-in still serves burgers.
Wilmington, IL · 10 min detourMilwaukee → Chicago
104 mi · 1.8h · easy leg
DAY 3
Friday, September 11
A short 1.8h drive from Milwaukee sets up the day. First pitch at 2:20 PM ET — Chicago Cubs vs. Pittsburgh Pirates at Wrigley Field today — Cubs Math Education Event today. Gemini Giant Wilmington is worth 10 minutes off the highway.
Stop 02 of 02
Chicago, IL · Fri Sep 11
Wrigley Field
Chicago Cubs · MLB
2:20 PM ET
vs. Pittsburgh Pirates
Must Eat at the Park
Chicago-Style Hot Dog
A Vienna beef hot dog on a poppy seed bun, dragged through the garden: yellow mustard, bright green relish, onions, tomato wedges, a pickle spear, sport peppers, and celery salt. No ketchup. Ever.
Local Beer
Old Style Lager
Served at Wrigley since 1950. The single most identified brand with Cubs baseball. The bleachers run on Old Style.
Pabst Brewing
The Friendly Confines and the Longest Drought in Sports
Pilgrim Notes · Chicago Baseball History
What to Budget
Estimates only — prices vary by availability
Tickets · 2 games (avg $46)$92
Hotels · 2 nights (avg $155)$310
Fuel · 104 mi at $0.18/mi$19
Ballpark food & drinks$100
Total Estimate$521
* Estimates only. Prices vary.
How This Trip Was Planned
Our Algorithm
We evaluate many stop orders (up to seven parks: every permutation; larger trips: smart samples plus nearest-neighbor paths from home) and keep the version that preserves the most ballparks on your list with the least driving between games, inside an expanded or standard date ...