Rental Car
Pick Up Your Rental
Pick upChicago · May 22
Drop offMilwaukee · May 26
Total miles734 mi
Getting There · Step 1
Stay Tonight · Chicago, IL
Hotel
Chicago Overnight
Check-inFri, May 22
Check-outSat, May 23
First pitch2:20 PM ET
Book near downtown or the ballpark so your first-game arrival stays simple.
DAY 1
Friday, May 22
First pitch at 2:20 PM ET — Chicago Cubs vs. Houston Astros at Wrigley Field today. Don't leave without Chicago-Style Hot Dog.
Stop 01 of 04
Chicago, IL · Fri May 22
Wrigley Field
Chicago Cubs · MLB
2:20 PM ET
vs. Houston Astros
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
Stay Tonight · Chicago, IL
Chicago Overnight
Check-inFri, May 22
Check-outSat, May 23
First pitch tomorrow at 7:15 PM ET. Leave by 12:19 PM.
Sat Morning
When to Depart
Leave by12:19 PM
Drive to Cincinnati315 mi · 5.4h
Game time7:15 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-65 S to IN-43, Chauncey Hill, W Lafayette
Midway Fuel-Up
Triple XXX Family Restaurant
West Lafayette, IN since 1929. Diner on the Purdue University strip open for nearly 100 years. The Duane Purvis All-American burger (peanut butter on a burger) is the reason people stop here. Sounds wrong. Is right.
Duane Purvis All-American burger
Open 7 AM–10 PM daily
Worth the Detour · +10 min
Tower of VW Bugs
Five colorfully painted 1960s Volkswagen Beetles stacked on top of each other in a pawn shop parking lot in Defiance. A mannequin climbs out of the fourth one. This is art.
Defiance, OH · 10 min detourChicago → Cincinnati
315 mi · 5.4h · regional run
DAY 2
Saturday, May 23
Chicago to Cincinnati is 5.4h — a solid drive, so leave early and plan a stop along the way. First pitch at 7:15 PM ET — Cincinnati Reds vs. St. Louis Cardinals at Great American Ball Park tonight — Bobblehead Giveaway (TBD) tonight. Tower of VW Bugs is worth 10 minutes off the highway.
Stop 02 of 04
Cincinnati, OH · Sat May 23
Great American Ball Park
Cincinnati Reds · MLB
7:15 PM ET
vs. St. Louis Cardinals
Must Eat at the Park
Cincinnati Chili Dog (Skyline)
Cincinnati chili served over a hot dog (the Cheese Coney). Skyline Chili has operated in Cincinnati since 1949.
Local Beer
MadTree Axis IPA
Cincinnati's most celebrated craft brewery. Axis IPA is their flagship.
MadTree Brewing
The Big Red Machine
Pilgrim Notes · Cincinnati Baseball History
Stay Tonight · Cincinnati, OH
Cincinnati Overnight
Check-inSat, May 23
Check-outSun, May 24
First pitch tomorrow at 2:10 PM ET. Leave by 7:16 AM.
Mon Morning
When to Depart
Leave by7:16 AM
Drive to Chicago313 mi · 5.4h
Game time2:10 PM ET
Leave on time to allow for fuel, food, and parking.
Breakfast Stop · Cincinnati, OH
Before You Hit the Road
Price Hill Chili
Price Hill neighborhood. Cincinnati chili for breakfast is the move — a 3-way at 8 AM has no business working and yet it does. Open early for the pre-work crowd.
3-Way chili + coffee
Open 7 AM Mon–Sat
Worth the Detour · +10 min
Tower of VW Bugs
Five colorfully painted 1960s Volkswagen Beetles stacked on top of each other in a pawn shop parking lot in Defiance. A mannequin climbs out of the fourth one. This is art.
Defiance, OH · 10 min detourCincinnati → Chicago
313 mi · 5.4h · regional run
DAY 4
Monday, May 25
Cincinnati to Chicago is 5.4h — a solid drive, so leave early and plan a stop along the way. First pitch at 2:10 PM ET — Chicago White Sox vs. Minnesota Twins at Guaranteed Rate Field today — Chase Meidroth Bobblehead today. Tower of VW Bugs is worth 10 minutes off the highway.
Stop 03 of 04
Chicago, IL · Mon May 25
Guaranteed Rate Field
Chicago White Sox · MLB
2:10 PM ET
vs. Minnesota Twins
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-inMon, May 25
Check-outTue, May 26
First pitch tomorrow at 7:40 PM ET. Leave by 4:20 PM.
Tue 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
Lou Mitchell's
Jackson Blvd since 1923. A Chicago institution older than most Wrigley Field renovations. Double-yolk eggs, homemade marmalade, complimentary Milk Duds while you wait. Cubs and Sox fans both claim it.
Double-yolk omelette + fresh OJ
Open 5:30 AM–3 PM Mon–Sat
Lunch Stop · I-94 N, Exit 344, Kenosha
Midway Fuel-Up
Brat Stop
Kenosha, WI on I-94. The Wisconsin welcome mat between Chicago and Milwaukee. Beer-soaked bratwurst grilled and served with sauerkraut and Stadium Sauce. The German heritage of the I-94 corridor in sandwich form.
Bratwurst + sauerkraut + Stadium Sauce
Open 11 AM–10 PM 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 detourChicago → Milwaukee
106 mi · 1.8h · easy leg
DAY 5
Tuesday, May 26
A short 1.8h drive from Chicago sets up the day. First pitch at 7:40 PM ET — Milwaukee Brewers vs. St. Louis Cardinals at American Family Field tonight. Gemini Giant Wilmington is worth 10 minutes off the highway.
Stop 04 of 04
Milwaukee, WI · Tue May 26
American Family Field
Milwaukee Brewers · MLB
7:40 PM ET
vs. St. Louis Cardinals
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
Shift 2 days to catch Ryne Sandberg Bobblehead (150th Anniversary) at Wrigley Field.
• Ryne Sandberg Bobblehead (150th Anniversary) at Wrigley Field
• Chase Meidroth Bobblehead at Rate Field
• Kyle Teel & Edgar Quero Dual Bobblehead at Rate Field
What to Budget
Estimates only — prices vary by availability
Tickets · 4 games (avg $46)$184
Hotels · 4 nights (avg $155)$620
Fuel · 734 mi at $0.18/mi$132
Ballpark food & drinks$200
Total Estimate$1,136
* 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 ...