Rental Car
Pick Up Your Rental
Pick upChicago · May 5
Drop offBoston · May 10
Total miles1175 mi
Getting There · Step 1
Stay Tonight · Chicago, IL
Hotel
Chicago Overnight
Check-inTue, May 5
Check-outWed, May 6
First pitch7:40 PM ET
Book near downtown or the ballpark so your first-game arrival stays simple.
DAY 1
Tuesday, May 5
First pitch at 7:40 PM ET — Chicago Cubs vs. Cincinnati Reds at Wrigley Field tonight. Don't leave without Chicago-Style Hot Dog.
Stop 01 of 03
Chicago, IL · Tue May 5
Wrigley Field
Chicago Cubs · MLB
7:40 PM ET
vs. Cincinnati Reds
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-inTue, May 5
Check-outWed, May 6
First pitch tomorrow at 7:40 PM ET. Leave by 4:22 PM.
Fri Morning
When to Depart
Leave by4:22 PM
Drive to Milwaukee104 mi · 1.8h
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
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
104 mi · 1.8h · easy leg
DAY 4
Friday, May 8
First pitch at 7:40 PM ET — Milwaukee Brewers vs. New York Yankees at American Family Field tonight. Gemini Giant Wilmington is worth 10 minutes off the highway.
Stop 02 of 03
Milwaukee, WI · Fri May 8
American Family Field
Milwaukee Brewers · MLB
7:40 PM ET
vs. New York Yankees
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-inFri, May 8
Check-outSat, May 9
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 Boston1071 mi · 18.5h
Game time1:35 PM ET
Long drive — consider stopping overnight in Milwaukee overnight.
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
Big Metal Dragon
A fire-breathing steel sculpture rises from a field beside Route 20 near East Bethany. Private property, but clearly visible from the road and absolutely baffling.
East Bethany, NY · 10 min detourMilwaukee → Boston
1071 mi · 18.5h · long haul
DAY 6
Sunday, May 10
It's a 18.5h haul from Milwaukee — plan to break this into two days or drive the night before. First pitch at 1:35 PM ET — Boston Red Sox vs. Tampa Bay Rays at Fenway Park today — Moms and Kids Run the Bases today. Big Metal Dragon is worth 10 minutes off the highway.
Stop 03 of 03
Boston, MA · Sun May 10
Fenway Park
Boston Red Sox · MLB
1:35 PM ET
vs. Tampa Bay Rays
Must Eat at the Park
Fenway Frank
The Fenway Frank has been a staple since the 1900s. A boiled-then-grilled Kayem hot dog in a New England-style bun, served with mustard and relish.
Local Beer
Sam Adams Boston Lager
The hometown craft brewery. Sam Adams Pavilion on the right field roof deck is the premium destination.
Boston Beer Company
The Green Monster and the Curse That Was Never Real
Pilgrim Notes · Boston Baseball History
Shift 2 days to catch Moms and Kids Run the Bases at Fenway Park.
• Moms and Kids Run the Bases at Fenway Park
• ONE PIECE Theme Night at Fenway Park
• The Housemaid Night at Fenway Park
What to Budget
Estimates only — prices vary by availability
Tickets · 3 games (avg $46)$138
Hotels · 5 nights (avg $155)$775
Fuel · 1175 mi at $0.18/mi$212
Ballpark food & drinks$150
Total Estimate$1,275
* 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 ...