Rental Car
Pick Up Your Rental
Pick upPittsburgh · Sep 1
Drop offSt. Louis · Sep 11
Total miles1148 mi
Getting There · Step 1
Stay Tonight · Pittsburgh, PA
Hotel
Pittsburgh Overnight
Check-inTue, Sep 1
Check-outWed, Sep 2
First pitch6:40 PM ET
Book near downtown or the ballpark so your first-game arrival stays simple.
DAY 1
Tuesday, September 1
First pitch at 6:40 PM ET — Pittsburgh Pirates vs. San Francisco Giants at PNC Park tonight. Don't leave without Primanti Brothers Sandwich.
Stop 01 of 05
Pittsburgh, PA · Tue Sep 1
PNC Park
Pittsburgh Pirates · MLB
6:40 PM ET
vs. San Francisco Giants
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, Sep 1
Check-outWed, Sep 2
First pitch tomorrow at 12:40 PM ET. Leave by 5:38 AM.
Wed Morning
When to Depart
Leave by5:38 AM
Drive to Cincinnati321 mi · 5.5h
Game time12:40 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
Lunch Stop · I-77 S to OH-7, Marietta Downtown
Midway Fuel-Up
Marietta Soda Luncheonette
Downtown Marietta, OH — the oldest settlement in the Northwest Territory, founded 1788. The Ohio River at your feet, a proper diner lunch, and a short walk to the historic Mound Cemetery. Perfect midpoint on the Pittsburgh–Cincinnati drive.
Daily soup + sandwich + soda fountain
Open 11 AM–3 PM Mon–Sat
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 detourPittsburgh → Cincinnati
321 mi · 5.5h · regional run
DAY 2
Wednesday, September 2
Pittsburgh to Cincinnati is 5.5h — a solid drive, so leave early and plan a stop along the way. First pitch at 12:40 PM ET — Cincinnati Reds vs. San Diego Padres at Great American Ball Park today. Field of Corn (Cornhenge) is worth 10 minutes off the highway.
Stop 02 of 05
Cincinnati, OH · Wed Sep 2
Great American Ball Park
Cincinnati Reds · MLB
12:40 PM ET
vs. San Diego Padres
Must Eat at the Park
Cincinnati Chili Dog (Skyline)
Cincinnati chili served over a hot dog (the Cheese Coney). Skyline Chili has operated in Cincinnati since 1949.
Local Beer
MadTree Axis IPA
Cincinnati's most celebrated craft brewery. Axis IPA is their flagship.
MadTree Brewing
The Big Red Machine
Pilgrim Notes · Cincinnati Baseball History
Stay Tonight · Cincinnati, OH
Cincinnati Overnight
Check-inWed, Sep 2
Check-outThu, Sep 3
First pitch tomorrow at 7:40 PM ET. Leave by 12:46 PM.
Fri Morning
When to Depart
Leave by12:46 PM
Drive to Chicago313 mi · 5.4h
Game time7:40 PM ET
Leave on time to allow for fuel, food, and parking.
Breakfast Stop · Cincinnati, OH
Before You Hit the Road
Price Hill Chili
Price Hill neighborhood. Cincinnati chili for breakfast is the move — a 3-way at 8 AM has no business working and yet it does. Open early for the pre-work crowd.
3-Way chili + coffee
Open 7 AM Mon–Sat
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 detourCincinnati → Chicago
313 mi · 5.4h · regional run
DAY 4
Friday, September 4
Cincinnati to Chicago is 5.4h — a solid drive, so leave early and plan a stop along the way. First pitch at 7:40 PM ET — Chicago White Sox vs. Minnesota Twins at Guaranteed Rate Field tonight. Tower of VW Bugs is worth 10 minutes off the highway.
Stop 03 of 05
Chicago, IL · Fri Sep 4
Guaranteed Rate Field
Chicago White Sox · MLB
7:40 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-inFri, Sep 4
Check-outSat, Sep 5
First pitch tomorrow at 2:10 PM ET. Leave by 10:50 AM.
Mon Morning
When to Depart
Leave by10:50 AM
Drive to Milwaukee106 mi · 1.8h
Game time2:10 PM ET
Leave on time to allow for fuel, food, and parking.
Breakfast Stop · Chicago, IL
Before You Hit the Road
Lou Mitchell's
Jackson Blvd since 1923. A Chicago institution older than most Wrigley Field renovations. Double-yolk eggs, homemade marmalade, complimentary Milk Duds while you wait. Cubs and Sox fans both claim it.
Double-yolk omelette + fresh OJ
Open 5:30 AM–3 PM Mon–Sat
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
106 mi · 1.8h · easy leg
DAY 7
Monday, September 7
First pitch at 2:10 PM ET — Milwaukee Brewers vs. Chicago Cubs at American Family Field today. Gemini Giant Wilmington is worth 10 minutes off the highway.
Stop 04 of 05
Milwaukee, WI · Mon Sep 7
American Family Field
Milwaukee Brewers · MLB
2:10 PM ET
vs. Chicago Cubs
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-inMon, Sep 7
Check-outTue, Sep 8
First pitch tomorrow at 8:15 PM ET. Leave by 11:43 AM.
Fri Morning
When to Depart
Leave by11:43 AM
Drive to St. Louis408 mi · 7h
Game time8:15 PM ET
Long drive — consider stopping overnight in St. Louis.
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 → St. Louis
408 mi · 7h · regional run
DAY 11
Friday, September 11
First pitch at 8:15 PM ET — St. Louis Cardinals vs. Chicago White Sox at Busch Stadium tonight. Gemini Giant Wilmington is worth 10 minutes off the highway.
Stop 05 of 05
St. Louis, MO · Fri Sep 11
Busch Stadium
St. Louis Cardinals · MLB
8:15 PM ET
vs. Chicago White Sox
Must Eat at the Park
St. Louis-Style Toasted Ravioli
Pasta filled with meat, breaded and deep-fried, served with marinara dipping sauce — a St. Louis original.
Local Beer
Busch Beer
The stadium is literally named for this beer. Historically appropriate in every way.
Anheuser-Busch
Musial, Gibson, and the Cardinal Way
Pilgrim Notes · St. Louis Baseball History
What to Budget
Estimates only — prices vary by availability
Tickets · 5 games (avg $46)$230
Hotels · 10 nights (avg $155)$1,550
Fuel · 1148 mi at $0.18/mi$207
Ballpark food & drinks$250
Total Estimate$2,237
* 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 ...