Rental Car
Pick Up Your Rental
Pick upChicago · Jul 24
Drop offCleveland · Aug 1
Total miles302 mi
Getting There · Step 1
Stay Tonight · Chicago, IL
Hotel
Chicago Overnight
Check-inFri, Jul 24
Check-outSat, Jul 25
First pitch7:40 PM ET
Book near downtown or the ballpark so your first-game arrival stays simple.
DAY 1
Friday, July 24
First pitch at 7:40 PM ET — Chicago White Sox vs. Houston Astros at Guaranteed Rate Field tonight. Don't leave without Maxwell Street Polish Sausage.
Stop 01 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 2:20 PM ET. Leave by 12:47 PM.
Fri Morning
When to Depart
Leave by12:47 PM
Drive to Chicago3 mi · 0.1h
Game time2:20 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 8
Friday, July 31
First pitch at 2:20 PM ET — Chicago Cubs vs. New York Yankees at Wrigley Field today. Gemini Giant Wilmington is worth 10 minutes off the highway.
Stop 02 of 03
Chicago, IL · Fri Jul 31
Wrigley Field
Chicago Cubs · MLB
2:20 PM ET
vs. New York Yankees
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-inFri, Jul 31
Check-outSat, Aug 1
First pitch tomorrow at 7:15 PM ET. Leave by 12:36 PM.
Sat Morning
When to Depart
Leave by12:36 PM
Drive to Cleveland299 mi · 5.2h
Game time7:15 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
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 → Cleveland
299 mi · 5.2h · regional run
DAY 9
Saturday, August 1
Chicago to Cleveland is 5.2h — a solid drive, so leave early and plan a stop along the way. First pitch at 7:15 PM ET — Cleveland Guardians vs. Arizona Diamondbacks at Progressive Field tonight — Cade Smith Bobblehead tonight. Tower of VW Bugs is worth 10 minutes off the highway.
Stop 03 of 03
Cleveland, OH · Sat Aug 1
Progressive Field
Cleveland Guardians · MLB
7:15 PM ET
vs. Arizona Diamondbacks
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
Shift 2 days to catch City Connect Warmup Jacket at Rate Field.
• City Connect Warmup Jacket at Rate Field
• Cade Smith Bobblehead at Progressive Field
What to Budget
Estimates only — prices vary by availability
Tickets · 3 games (avg $46)$138
Hotels · 8 nights (avg $155)$1,240
Fuel · 302 mi at $0.18/mi$54
Ballpark food & drinks$150
Total Estimate$1,582
* 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 ...