Rental Car
Pick Up Your Rental
Pick upCleveland · Jun 14
Drop offChicago · Jun 22
Total miles424 mi
Getting There · Step 1
Stay Tonight · Cleveland, OH
Hotel
Cleveland Overnight
Check-inSun, Jun 14
Check-outMon, Jun 15
First pitch1:40 PM ET
Book near downtown or the ballpark so your first-game arrival stays simple.
DAY 1
Sunday, June 14
First pitch at 1:40 PM ET — Cleveland Guardians vs. Detroit Tigers at Progressive Field today. Don't leave without Polish Boy Sausage.
Stop 01 of 03
Cleveland, OH · Sun Jun 14
Progressive Field
Cleveland Guardians · MLB
1:40 PM ET
vs. Detroit Tigers
Must Eat at the Park
Polish Boy Sausage
A kielbasa in a bun topped with french fries, coleslaw, and hot sauce. A Cleveland original found nowhere else.
Local Beer
Great Lakes Dortmunder Gold
The Cleveland craft institution. Dortmunder Gold has won more awards than any Ohio beer.
Great Lakes Brewing
The Longest Championship Drought and One Perfect Game
Pilgrim Notes · Cleveland Baseball History
Stay Tonight · Cleveland, OH
Cleveland Overnight
Check-inSun, Jun 14
Check-outMon, Jun 15
First pitch tomorrow at 7:40 PM ET. Leave by 12:41 PM.
Tue Morning
When to Depart
Leave by12:41 PM
Drive to Milwaukee318 mi · 5.5h
Game time7:40 PM ET
Leave on time to allow for fuel, food, and parking.
Breakfast Stop · Cleveland, OH
Before You Hit the Road
West Side Market
Ohio City since 1912. The greatest market hall in the Midwest. Over 100 vendors — pierogi, kielbasa, fresh bread. Grab breakfast from multiple stalls and eat in the main hall. A Cleveland essential.
Fresh pierogi + kielbasa + bread from multiple stalls
Open 7 AM Wed/Fri/Sat/Sun
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 detourCleveland → Milwaukee
318 mi · 5.5h · regional run
DAY 3
Tuesday, June 16
Cleveland to Milwaukee is 5.5h — a solid drive, so leave early and plan a stop along the way. First pitch at 7:40 PM ET — Milwaukee Brewers vs. Cleveland Guardians at American Family Field tonight. Tower of VW Bugs is worth 10 minutes off the highway.
Stop 02 of 03
Milwaukee, WI · Tue Jun 16
American Family Field
Milwaukee Brewers · MLB
7:40 PM ET
vs. Cleveland Guardians
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-inTue, Jun 16
Check-outWed, Jun 17
First pitch tomorrow at 7:40 PM ET. Leave by 4:20 PM.
Mon Morning
When to Depart
Leave by4:20 PM
Drive to Chicago106 mi · 1.8h
Game time7:40 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
106 mi · 1.8h · easy leg
DAY 9
Monday, June 22
First pitch at 7:40 PM ET — Chicago White Sox vs. Cleveland Guardians at Guaranteed Rate Field tonight. Gemini Giant Wilmington is worth 10 minutes off the highway.
Stop 03 of 03
Chicago, IL · Mon Jun 22
Guaranteed Rate Field
Chicago White Sox · MLB
7:40 PM ET
vs. Cleveland Guardians
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
What to Budget
Estimates only — prices vary by availability
Tickets · 3 games (avg $46)$138
Hotels · 8 nights (avg $155)$1,240
Fuel · 424 mi at $0.18/mi$76
Ballpark food & drinks$150
Total Estimate$1,604
* 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 ...