Rental Car
Pick Up Your Rental
Pick upMilwaukee · May 22
Drop offPittsburgh · May 26
Total miles659 mi
Getting There · Step 1
Stay Tonight · Milwaukee, WI
Hotel
Milwaukee Overnight
Check-inFri, May 22
Check-outSat, May 23
First pitch7:40 PM ET
Book near downtown or the ballpark so your first-game arrival stays simple.
DAY 1
Friday, May 22
First pitch at 7:40 PM ET — Milwaukee Brewers vs. Los Angeles Dodgers at American Family Field tonight. Don't leave without Wisconsin Brat (Klement's).
Stop 01 of 04
Milwaukee, WI · Fri May 22
American Family Field
Milwaukee Brewers · MLB
7:40 PM ET
vs. Los Angeles Dodgers
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-inFri, May 22
Check-outSat, May 23
First pitch tomorrow at 2:20 PM ET. Leave by 11:02 AM.
Sat 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 2
Saturday, May 23
A short 1.8h drive from Milwaukee sets up the day. First pitch at 2:20 PM ET — Chicago Cubs vs. Houston Astros at Wrigley Field today. Gemini Giant Wilmington is worth 10 minutes off the highway.
Stop 02 of 04
Chicago, IL · Sat May 23
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-inSat, May 23
Check-outSun, May 24
First pitch tomorrow at 6:10 PM ET. Leave by 11:31 AM.
Mon Morning
When to Depart
Leave by11:31 AM
Drive to Cleveland299 mi · 5.2h
Game time6:10 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
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 → Cleveland
299 mi · 5.2h · regional run
DAY 4
Monday, May 25
Chicago to Cleveland is 5.2h — a solid drive, so leave early and plan a stop along the way. First pitch at 6:10 PM ET — Cleveland Guardians vs. Washington Nationals at Progressive Field tonight — City Connect Plush Blanket tonight. Tower of VW Bugs is worth 10 minutes off the highway.
Stop 03 of 04
Cleveland, OH · Mon May 25
Progressive Field
Cleveland Guardians · MLB
6:10 PM ET
vs. Washington Nationals
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-inMon, May 25
Check-outTue, May 26
First pitch tomorrow at 6:40 PM ET. Leave by 12:45 PM.
Tue Morning
When to Depart
Leave by12:45 PM
Drive to Pittsburgh256 mi · 4.4h
Game time6:40 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
Lunch Stop · I-76/80 E, Mahoning Ave exit
Midway Fuel-Up
Simon's Deli
Youngstown. The triple-decker club that Rust Belt travelers have been stopping for on I-76.
Triple-decker club
Worth the Detour · +10 min
Zanesville Y-Bridge Ohio
The only Y-shaped bridge in the world. Cross it from any side, end up where you started.
Zanesville, OH · 10 min detourCleveland → Pittsburgh
256 mi · 4.4h · easy leg
DAY 5
Tuesday, May 26
Cleveland to Pittsburgh is 4.4h — a solid drive, so leave early and plan a stop along the way. First pitch at 6:40 PM ET — Pittsburgh Pirates vs. Chicago Cubs at PNC Park tonight. Zanesville Y-Bridge Ohio is worth 10 minutes off the highway.
Stop 04 of 04
Pittsburgh, PA · Tue May 26
PNC Park
Pittsburgh Pirates · MLB
6:40 PM ET
vs. Chicago Cubs
Must Eat at the Park
Primanti Brothers Sandwich
Pittsburgh's most iconic food in its natural habitat. Meat and cheese on airy Italian bread loaded with tomatoes, coleslaw, and french fries inside the sandwich. Designed for Pittsburgh truckers in 1933.
Local Beer
Fat Head's Bullpen Tap Bar
Eight rotating taps positioned directly above the Pirates bullpen. The only bar in baseball where you can watch a reliever warm up while drinking a Head Hunter IPA. Arrive before first pitch for a seat at the rail.
Fat Head's Brewery · North Olmsted, OH
Maz, Clemente, and the Most Beautiful View in Baseball
Pilgrim Notes · Pittsburgh Baseball History
Shift 2 days to catch Ryne Sandberg Bobblehead (150th Anniversary) at Wrigley Field.
• Ryne Sandberg Bobblehead (150th Anniversary) at Wrigley Field
• City Connect Plush Blanket at Progressive Field
• Drone Show #1 at PNC Park
• Austin Hedges Jersey Replica at Progressive Field
What to Budget
Estimates only — prices vary by availability
Tickets · 4 games (avg $46)$184
Hotels · 4 nights (avg $155)$620
Fuel · 659 mi at $0.18/mi$119
Ballpark food & drinks$200
Total Estimate$1,123
* 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 ...