Rental Car
Pick Up Your Rental
Pick upChicago · Sep 12
Drop offPittsburgh · Sep 18
Total miles867 mi
Getting There · Step 1
Stay Tonight · Chicago, IL
Hotel
Chicago Overnight
Check-inSat, Sep 12
Check-outSun, Sep 13
First pitch2:20 PM ET
Book near downtown or the ballpark so your first-game arrival stays simple.
DAY 1
Saturday, September 12
First pitch at 2:20 PM ET — Chicago Cubs vs. Pittsburgh Pirates at Wrigley Field today. Don't leave without Chicago-Style Hot Dog.
Stop 01 of 04
Chicago, IL · Sat Sep 12
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-inSat, Sep 12
Check-outSun, Sep 13
First pitch tomorrow at 6:40 PM ET. Leave by 11:44 AM.
Mon Morning
When to Depart
Leave by11:44 AM
Drive to Cincinnati315 mi · 5.4h
Game time6:40 PM ET
Long drive — consider stopping overnight in Cincinnati.
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-65 S to IN-43, Chauncey Hill, W Lafayette
Midway Fuel-Up
Triple XXX Family Restaurant
West Lafayette, IN since 1929. Diner on the Purdue University strip open for nearly 100 years. The Duane Purvis All-American burger (peanut butter on a burger) is the reason people stop here. Sounds wrong. Is right.
Duane Purvis All-American burger
Open 7 AM–10 PM 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 → Cincinnati
315 mi · 5.4h · regional run
DAY 3
Monday, September 14
Chicago to Cincinnati is 5.4h — a solid drive, so leave early and plan a stop along the way. First pitch at 6:40 PM ET — Cincinnati Reds vs. Los Angeles Dodgers at Great American Ball Park tonight. Tower of VW Bugs is worth 10 minutes off the highway.
Stop 02 of 04
Cincinnati, OH · Mon Sep 14
Great American Ball Park
Cincinnati Reds · MLB
6:40 PM ET
vs. Los Angeles Dodgers
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-inMon, Sep 14
Check-outTue, Sep 15
First pitch tomorrow at 1:10 PM ET. Leave by 6:34 AM.
Wed Morning
When to Depart
Leave by6:34 AM
Drive to Cleveland296 mi · 5.1h
Game time1:10 PM ET
Long drive — consider stopping overnight in Cleveland.
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
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 detourCincinnati → Cleveland
296 mi · 5.1h · regional run
DAY 5
Wednesday, September 16
Cincinnati to Cleveland is 5.1h — a solid drive, so leave early and plan a stop along the way. First pitch at 1:10 PM ET — Cleveland Guardians vs. Chicago White Sox at Progressive Field today. Field of Corn (Cornhenge) is worth 10 minutes off the highway.
Stop 03 of 04
Cleveland, OH · Wed Sep 16
Progressive Field
Cleveland Guardians · MLB
1:10 PM ET
vs. Chicago White Sox
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, Sep 16
Check-outThu, Sep 17
First pitch tomorrow at 6:40 PM ET. Leave by 12:45 PM.
Fri Morning
When to Depart
Leave by12:45 PM
Drive to Pittsburgh256 mi · 4.4h
Game time6:40 PM ET
Long drive — consider stopping overnight in Pittsburgh.
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 · Multiple I-76 exits across Western PA
Midway Fuel-Up
Eat'n Park
The Pittsburgh chain since 1949 that defines Western PA comfort food. The Smiley cookie is iconic but the burgers, soups, and pie are the real reasons to stop. The purest expression of Pittsburgh diner culture.
Superburger + soup + Smiley cookie
Open 6 AM–midnight daily
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 7
Friday, September 18
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. Kansas City Royals at PNC Park tonight. Zanesville Y-Bridge Ohio is worth 10 minutes off the highway.
Stop 04 of 04
Pittsburgh, PA · Fri Sep 18
PNC Park
Pittsburgh Pirates · MLB
6:40 PM ET
vs. Kansas City Royals
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
What to Budget
Estimates only — prices vary by availability
Tickets · 4 games (avg $46)$184
Hotels · 6 nights (avg $155)$930
Fuel · 867 mi at $0.18/mi$156
Ballpark food & drinks$200
Total Estimate$1,470
* 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 ...