Rental Car
Pick Up Your Rental
Pick upCleveland · Sep 6
Drop offMilwaukee · Sep 12
Total miles405 mi
Getting There · Step 1
Stay Tonight · Cleveland, OH
Hotel
Cleveland Overnight
Check-inSun, Sep 6
Check-outMon, Sep 7
First pitch1:40 PM ET
Book near downtown or the ballpark so your first-game arrival stays simple.
DAY 1
Sunday, September 6
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 04
Cleveland, OH · Sun Sep 6
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, Sep 6
Check-outMon, Sep 7
First pitch tomorrow at 7:40 PM ET. Leave by 1:02 PM.
Tue Morning
When to Depart
Leave by1:02 PM
Drive to Chicago298 mi · 5.1h
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 → Chicago
298 mi · 5.1h · regional run
DAY 3
Tuesday, September 8
Cleveland to Chicago is 5.1h — a solid drive, so leave early and plan a stop along the way. First pitch at 7:40 PM ET — Chicago White Sox vs. Pittsburgh Pirates at Guaranteed Rate Field tonight. Tower of VW Bugs is worth 10 minutes off the highway.
Stop 02 of 04
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 2:20 PM ET. Leave by 12:47 PM.
Fri Morning
When to Depart
Leave by12:47 PM
Drive to Chicago3 mi · 0.1h
Game time2:20 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
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 → Chicago
3 mi · 0.1h · easy leg
DAY 6
Friday, September 11
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 03 of 04
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
Stay Tonight · Chicago, IL
Chicago Overnight
Check-inFri, Sep 11
Check-outSat, Sep 12
First pitch tomorrow at 7:10 PM ET. Leave by 3:52 PM.
Sat Morning
When to Depart
Leave by3:52 PM
Drive to Milwaukee104 mi · 1.8h
Game time7:10 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 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
104 mi · 1.8h · easy leg
DAY 7
Saturday, September 12
A short 1.8h drive from Chicago sets up the day. First pitch at 7:10 PM ET — Milwaukee Brewers vs. Cincinnati Reds at American Family Field tonight — Oktoberfest Alpine Hat tonight. Gemini Giant Wilmington is worth 10 minutes off the highway.
Stop 04 of 04
Milwaukee, WI · Sat Sep 12
American Family Field
Milwaukee Brewers · MLB
7:10 PM ET
vs. Cincinnati Reds
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 Cubs Math Education Event at Wrigley Field.
• Cubs Math Education Event at Wrigley Field
• Oktoberfest Alpine Hat at American Family Field
• Kids Giveaway: Hank the Dog Plushie at American Family Field
• Sammy Sosa Bobblehead (150th Anniversary); Youth Baseball Sunglasses at Wrigley Field
What to Budget
Estimates only — prices vary by availability
Tickets · 4 games (avg $46)$184
Hotels · 6 nights (avg $155)$930
Fuel · 405 mi at $0.18/mi$73
Ballpark food & drinks$200
Total Estimate$1,387
* 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 ...