Rental Car
Pick Up Your Rental
Pick upChicago · Jul 22
Drop offPittsburgh · Jul 26
Total miles513 mi
Getting There · Step 1
Stay Tonight · Chicago, IL
Hotel
Chicago Overnight
Check-inWed, Jul 22
Check-outThu, Jul 23
First pitch8:05 PM ET
Book near downtown or the ballpark so your first-game arrival stays simple.
DAY 1
Wednesday, July 22
First pitch at 8:05 PM ET — Chicago Cubs vs. Detroit Tigers at Wrigley Field tonight. Don't leave without Chicago-Style Hot Dog.
Stop 01 of 03
Chicago, IL · Wed Jul 22
Wrigley Field
Chicago Cubs · MLB
8:05 PM ET
vs. Detroit Tigers
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-inWed, Jul 22
Check-outThu, Jul 23
First pitch tomorrow at 7:40 PM ET. Leave by 6:07 PM.
Fri Morning
When to Depart
Leave by6:07 PM
Drive to Chicago3 mi · 0.1h
Game time7:40 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
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 3
Friday, July 24
First pitch at 7:40 PM ET — Chicago White Sox vs. Houston Astros at Guaranteed Rate Field tonight. Gemini Giant Wilmington is worth 10 minutes off the highway.
Stop 02 of 03
Chicago, IL · Fri Jul 24
Guaranteed Rate Field
Chicago White Sox · MLB
7:40 PM ET
vs. Houston Astros
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, Jul 24
Check-outSat, Jul 25
First pitch tomorrow at 1:35 PM ET. Leave by Previous evening — overnight drive recommended.
Sun Morning
When to Depart
Leave byPrevious evening — overnight drive recommended
Drive to Pittsburgh510 mi · 8.8h
Game time1:35 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 5
Sunday, July 26
It's a 8.8h haul from Chicago — plan to break this into two days or drive the night before. First pitch at 1:35 PM ET — Pittsburgh Pirates vs. Chicago Cubs at PNC Park today — Yinzerpalooza Weekend: Kids Daniel Tiger Plush (14 & under) today. Field of Corn (Cornhenge) is worth 10 minutes off the highway.
Stop 03 of 03
Pittsburgh, PA · Sun Jul 26
PNC Park
Pittsburgh Pirates · MLB
1:35 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 Yinzerpalooza Weekend: Free T-Shirt Giveaway at PNC Park.
• Yinzerpalooza Weekend: Free T-Shirt Giveaway at PNC Park
• Yinzerpalooza Weekend: Bobblehead Giveaway (TBD) at PNC Park
• City Connect Warmup Jacket at Rate Field
• Yinzerpalooza Weekend: Kids Daniel Tiger Plush (14 & under) at PNC Park
What to Budget
Estimates only — prices vary by availability
Tickets · 3 games (avg $46)$138
Hotels · 4 nights (avg $155)$620
Fuel · 513 mi at $0.18/mi$92
Ballpark food & drinks$150
Total Estimate$1,000
* 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 ...