Rental Car
Pick Up Your Rental
Pick upMilwaukee · Aug 8
Drop offChicago · Aug 17
Total miles1482 mi
Getting There · Step 1
Stay Tonight · Milwaukee, WI
Hotel
Milwaukee Overnight
Check-inSat, Aug 8
Check-outSun, Aug 9
First pitch7:10 PM ET
Book near downtown or the ballpark so your first-game arrival stays simple.
DAY 1
Saturday, August 8
First pitch at 7:10 PM ET — Milwaukee Brewers vs. Minnesota Twins at American Family Field tonight — Brewers Bar Dice Set (21+ only) tonight.
Stop 01 of 06
Milwaukee, WI · Sat Aug 8
American Family Field
Milwaukee Brewers · MLB
7:10 PM ET
vs. Minnesota Twins
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-inSat, Aug 8
Check-outSun, Aug 9
First pitch tomorrow at 2:10 PM ET. Leave by 10:50 AM.
Sun Morning
When to Depart
Leave by10:50 AM
Drive to Chicago106 mi · 1.8h
Game time2:10 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
106 mi · 1.8h · easy leg
DAY 2
Sunday, August 9
A short 1.8h drive from Milwaukee sets up the day. First pitch at 2:10 PM ET — Chicago White Sox vs. Cleveland Guardians at Guaranteed Rate Field today. Gemini Giant Wilmington is worth 10 minutes off the highway.
Stop 02 of 06
Chicago, IL · Sun Aug 9
Guaranteed Rate Field
Chicago White Sox · MLB
2:10 PM ET
vs. Cleveland Guardians
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-inSun, Aug 9
Check-outMon, Aug 10
First pitch tomorrow at 6:10 PM ET. Leave by 11:16 AM.
Fri Morning
When to Depart
Leave by11:16 AM
Drive to Cincinnati313 mi · 5.4h
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
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
313 mi · 5.4h · regional run
DAY 7
Friday, August 14
First pitch at 6:10 PM ET — Cincinnati Reds vs. Miami Marlins at Great American Ball Park tonight — Fireworks Friday tonight. Tower of VW Bugs is worth 10 minutes off the highway.
Stop 03 of 06
Cincinnati, OH · Fri Aug 14
Great American Ball Park
Cincinnati Reds · MLB
6:10 PM ET
vs. Miami Marlins
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-inFri, Aug 14
Check-outSat, Aug 15
First pitch tomorrow at 7:10 PM ET. Leave by 12:34 PM.
Sat Morning
When to Depart
Leave by12:34 PM
Drive to Cleveland296 mi · 5.1h
Game time7:10 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
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 8
Saturday, August 15
Cincinnati to Cleveland is 5.1h — a solid drive, so leave early and plan a stop along the way. First pitch at 7:10 PM ET — Cleveland Guardians vs. San Diego Padres at Progressive Field tonight — City Connect Sling Bag tonight. Field of Corn (Cornhenge) is worth 10 minutes off the highway.
Stop 04 of 06
Cleveland, OH · Sat Aug 15
Progressive Field
Cleveland Guardians · MLB
7:10 PM ET
vs. San Diego Padres
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-inSat, Aug 15
Check-outSun, Aug 16
First pitch tomorrow at 1:35 PM ET. Leave by 7:40 AM.
Sun Morning
When to Depart
Leave by7:40 AM
Drive to Pittsburgh256 mi · 4.4h
Game time1:35 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 · 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 9
Sunday, August 16
Cleveland to Pittsburgh is 4.4h — a solid drive, so leave early and plan a stop along the way. First pitch at 1:35 PM ET — Pittsburgh Pirates vs. Boston Red Sox at PNC Park today. Zanesville Y-Bridge Ohio is worth 10 minutes off the highway.
Stop 05 of 06
Pittsburgh, PA · Sun Aug 16
PNC Park
Pittsburgh Pirates · MLB
1:35 PM ET
vs. Boston Red Sox
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-inSun, Aug 16
Check-outMon, Aug 17
First pitch tomorrow at 8:05 PM ET. Leave by 9:46 AM.
Mon Morning
When to Depart
Leave by9:46 AM
Drive to Chicago511 mi · 8.8h
Game time8:05 PM ET
Long drive — consider stopping overnight in Pittsburgh overnight.
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-71 N to I-75 N, Covington KY exit
Midway Fuel-Up
Skyline Chili Covington
The Cincinnati-area Skyline Chili location just off I-71/75 on the Pittsburgh to Chicago corridor. Cincinnati chili on spaghetti with shredded cheddar — a 3-Way — is one of the great regional American dishes. This is the correct stop at the midpoint of this drive.
3-Way chili + oyster crackers + coffee
Open 10 AM–10 PM 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 detourPittsburgh → Chicago
511 mi · 8.8h · long haul
DAY 10
Monday, August 17
It's a 8.8h haul from Pittsburgh — plan to break this into two days or drive the night before. First pitch at 8:05 PM ET — Chicago Cubs vs. Chicago White Sox at Wrigley Field tonight. Field of Corn (Cornhenge) is worth 10 minutes off the highway.
Stop 06 of 06
Chicago, IL · Mon Aug 17
Wrigley Field
Chicago Cubs · MLB
8:05 PM ET
vs. Chicago White Sox
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
Shift 2 days to catch Fireworks Friday at Great American Ball Park.
• Fireworks Friday at Great American Ball Park
• Bobblehead Giveaway (TBD) at Great American Ball Park
• City Connect Sling Bag at Progressive Field
What to Budget
Estimates only — prices vary by availability
Tickets · 6 games (avg $46)$276
Hotels · 9 nights (avg $155)$1,395
Fuel · 1482 mi at $0.18/mi$267
Ballpark food & drinks$300
Total Estimate$2,238
* 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 ...