Rental Car
Pick Up Your Rental
Pick upChicago · Sep 8
Drop offMilwaukee · Sep 9
Total miles106 mi
Getting There · Step 1
Stay Tonight · Chicago, IL
Hotel
Chicago Overnight
Check-inTue, Sep 8
Check-outWed, Sep 9
First pitch7:40 PM ET
Book near downtown or the ballpark so your first-game arrival stays simple.
DAY 1
Tuesday, September 8
First pitch at 7:40 PM ET — Chicago White Sox vs. Pittsburgh Pirates at Guaranteed Rate Field tonight. Don't leave without Maxwell Street Polish Sausage.
Stop 01 of 02
Chicago, IL · Tue Sep 8
Guaranteed Rate Field
Chicago White Sox · MLB
7:40 PM ET
vs. Pittsburgh Pirates
Must Eat at the Park
Maxwell Street Polish Sausage
Jim's Original Maxwell Street Polish — a grilled Polish sausage with mustard and grilled onions on a bun.
Local Beer
Revolution Anti-Hero IPA
Chicago's largest independent craft brewery also serves the South Side.
Revolution Brewing
The Friendly Confines and the Longest Drought in Sports
Pilgrim Notes · Chicago Baseball History
Stay Tonight · Chicago, IL
Chicago Overnight
Check-inTue, Sep 8
Check-outWed, Sep 9
First pitch tomorrow at 7:40 PM ET. Leave by 4:20 PM.
Wed Morning
When to Depart
Leave by4:20 PM
Drive to Milwaukee106 mi · 1.8h
Game time7:40 PM ET
Leave on time to allow for fuel, food, and parking.
Breakfast Stop · Chicago, IL
Before You Hit the Road
Ann Sather
Boystown since 1945. The cinnamon rolls are mythological — the size of your head, fresh every morning. Swedish-American diner that has defined Wrigleyville breakfast culture for 80 years.
Giant cinnamon roll + eggs
Open 7 AM daily
Lunch Stop · I-94 N Exit 342
Midway Fuel-Up
Frank's Diner
Classic Wisconsin diner on I-94 northbound. The Locomotive has been fueling road trippers for decades.
Locomotive Burger — everything on it
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 detourChicago → Milwaukee
106 mi · 1.8h · easy leg
DAY 2
Wednesday, September 9
A short 1.8h drive from Chicago sets up the day. First pitch at 7:40 PM ET — Milwaukee Brewers vs. Chicago Cubs at American Family Field tonight. Gemini Giant Wilmington is worth 10 minutes off the highway.
Stop 02 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
What to Budget
Estimates only — prices vary by availability
Tickets · 2 games (avg $46)$92
Hotels · 1 nights (avg $155)$155
Fuel · 106 mi at $0.18/mi$19
Ballpark food & drinks$100
Total Estimate$366
* 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 ...