Rental Car
Pick Up Your Rental
Pick upMilwaukee · May 22
Drop offPittsburgh · May 27
Total miles617 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 2:10 PM ET. Leave by 12:37 PM.
Mon Morning
When to Depart
Leave by12:37 PM
Drive to Chicago3 mi · 0.1h
Game time2:10 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
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 4
Monday, May 25
First pitch at 2:10 PM ET — Chicago White Sox vs. Minnesota Twins at Guaranteed Rate Field today — Chase Meidroth Bobblehead today. Gemini Giant Wilmington 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 6:40 PM ET. Leave by 8:22 AM.
Wed Morning
When to Depart
Leave by8:22 AM
Drive to Pittsburgh510 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
510 mi · 8.8h · long haul
DAY 6
Wednesday, May 27
It's a 8.8h haul from Chicago — plan to break this into two days or drive the night before. First pitch at 6:40 PM ET — Pittsburgh Pirates vs. Chicago Cubs at PNC Park tonight. Field of Corn (Cornhenge) is worth 10 minutes off the highway.
Stop 04 of 04
Pittsburgh, PA · Wed May 27
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
• Chase Meidroth Bobblehead at Rate Field
• Drone Show #1 at PNC Park
• 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 · 5 nights (avg $155)$775
Fuel · 617 mi at $0.18/mi$111
Ballpark food & drinks$200
Total Estimate$1,270
* 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 ...