Rental Car
Pick Up Your Rental
Pick upChicago · Jun 2
Drop offMilwaukee · Jun 12
Total miles1085 mi
Getting There · Step 1
Stay Tonight · Chicago, IL
Hotel
Chicago Overnight
Check-inTue, Jun 2
Check-outWed, Jun 3
First pitch8:05 PM ET
Book near downtown or the ballpark so your first-game arrival stays simple.
DAY 1
Tuesday, June 2
First pitch at 8:05 PM ET — Chicago Cubs vs. Athletics at Wrigley Field tonight — ALS Awareness T-Shirt tonight.
Stop 01 of 04
Chicago, IL · Tue Jun 2
Wrigley Field
Chicago Cubs · MLB
8:05 PM ET
vs. Athletics
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-inTue, Jun 2
Check-outWed, Jun 3
First pitch tomorrow at 6:40 PM ET. Leave by 8:21 AM.
Tue Morning
When to Depart
Leave by8:21 AM
Drive to Pittsburgh511 mi · 8.8h
Game time6:40 PM ET
Long drive — consider stopping overnight in Chicago overnight.
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
Field of Corn (Cornhenge)
109 concrete ears of corn arranged in rows like Arlington National Cemetery outside Columbus. Each one weighs 1,500 lbs and stands 6 feet tall. There is no satisfying explanation.
Dublin, OH · 10 min detourChicago → Pittsburgh
511 mi · 8.8h · long haul
DAY 8
Tuesday, June 9
First pitch at 6:40 PM ET — Pittsburgh Pirates vs. Los Angeles Dodgers at PNC Park tonight. Field of Corn (Cornhenge) is worth 10 minutes off the highway.
Stop 02 of 04
Pittsburgh, PA · Tue Jun 9
PNC Park
Pittsburgh Pirates · MLB
6:40 PM ET
vs. Los Angeles Dodgers
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
Stay Tonight · Pittsburgh, PA
Pittsburgh Overnight
Check-inTue, Jun 9
Check-outWed, Jun 10
First pitch tomorrow at 1:10 PM ET. Leave by 7:15 AM.
Wed Morning
When to Depart
Leave by7:15 AM
Drive to Cleveland256 mi · 4.4h
Game time1:10 PM ET
Leave on time to allow for fuel, food, and parking.
Breakfast Stop · Pittsburgh, PA
Before You Hit the Road
Pamela's Diner
Multiple locations. Obama ordered here on the campaign trail. The hotcakes are thin, buttery, perfect.
Crepe-style hotcakes
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 detourPittsburgh → Cleveland
256 mi · 4.4h · easy leg
DAY 9
Wednesday, June 10
Pittsburgh to Cleveland is 4.4h — a solid drive, so leave early and plan a stop along the way. First pitch at 1:10 PM ET — Cleveland Guardians vs. New York Yankees at Progressive Field today. Zanesville Y-Bridge Ohio is worth 10 minutes off the highway.
Stop 03 of 04
Cleveland, OH · Wed Jun 10
Progressive Field
Cleveland Guardians · MLB
1:10 PM ET
vs. New York Yankees
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-inWed, Jun 10
Check-outThu, Jun 11
First pitch tomorrow at 7:40 PM ET. Leave by 12:41 PM.
Fri 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 11
Friday, June 12
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. Philadelphia Phillies at American Family Field tonight — Pride Night tonight. Tower of VW Bugs is worth 10 minutes off the highway.
Stop 04 of 04
Milwaukee, WI · Fri Jun 12
American Family Field
Milwaukee Brewers · MLB
7:40 PM ET
vs. Philadelphia Phillies
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 Puerto Rican Heritage Jersey at Wrigley Field.
• Puerto Rican Heritage Jersey at Wrigley Field
• Wrigley Field Replica Ballpark at Wrigley Field
• Pride Night: Zambelli Fireworks Night #3 at PNC Park
• Free T-Shirt at Progressive Field
What to Budget
Estimates only — prices vary by availability
Tickets · 4 games (avg $46)$184
Hotels · 10 nights (avg $155)$1,550
Fuel · 1085 mi at $0.18/mi$195
Ballpark food & drinks$200
Total Estimate$2,129
* 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 ...