The state’s best hiking, a straight shot southwest.
Major-week road trip guide
Presidents Cup 2026
Team match play in the western Chicago suburbs, with early-fall driving weather and the canyons, lake towns, and river bluffs of the region wide open.
Part of the Presidents Cup series - see every year →When to book
42 days out- Plan6–12 mo out
- Book3–6 mo out
- Lock infinal 6–10 wk
- On the groundevent week
Crunch time. Rooms near the venue are getting thin — if they’re gone, stay an hour out and drive in scenic. Lock it this week.
Straight talk: “book now or it’s gone” gets overstated. We flag both surge risk and the cooldown deals when a market runs soft.
Host-state Gem Hunt
Help decide the detours fans should not miss.
Why this trip works
Built around real travel intent.
Golf fans staying around Chicago who want a fall-color detour instead of a third night downtown.
A Wisconsin lake-town day just over the border.
Bluffs and a historic main street out west.
Worth the slack day
Presidents Cup side quests.
Vote the Illinois and Wisconsin gems near Medinah and build the autumn drive around the matches.
Starved Rock State Park
fall-color canyons for an off day
Lake Geneva
lakeshore path and resort town over the line
Galena
Mississippi bluff town for a slower drive
Where to eat
Restaurants around Presidents Cup.
In town for the golf: the full Chicago food map, from deep dish and Italian beef to steakhouses and neighborhood gems.
Venue focus: Medinah and the Chicago metro
Little Italy$
Al's Italian BeefThe Taylor Street original that helped invent the Chicago Italian beef.
Order: Italian beef, hot and dipped
Lincoln Park$$$$
AlineaOne of America's most celebrated tasting-menu destinations.
Order: Seasonal tasting menu
West Loop$$$
Au ChevalThe diner-style spot behind what's called the best cheeseburger in America.
Order: Double cheeseburger
River North$$$$
Bavette's Bar & BoeufIntimate 1920s-speakeasy-styled steakhouse with a devoted following.
Order: Dry-aged ribeye
Uptown$$
DemeraChicago's top-rated Ethiopian, communal platters and honey wine.
Order: Combination platter
River North$$$
Gene & GeorgettiOld-school 1941 steakhouse pairing aged steaks with Italian classics.
Order: Chicken Vesuvio
Gold Coast$$$$
Gibsons Bar & SteakhouseA Chicago rite of passage for martinis, big steaks, and people-watching.
Order: Bone-in ribeye
Fulton Market$$$
Girl & the GoatStephanie Izard's boisterous flagship of bold small plates.
Order: Wood-fired pork shoulder
Chicago$$
Greek IslandsA white-tablecloth Greektown staple since 1971.
Order: Saganaki
Ukrainian Village$$$$
KasamaThe world's first Michelin-two-star Filipino restaurant.
Order: Chicken adobo
Chinatown$$
Lao Sze ChuanChef Tony Hu's 1998 original, a beloved Sichuan restaurant.
Order: Dry-chili chicken
Chatham$
Lem's Bar-B-QA no-frills South Side institution since 1954 famous for rib tips.
Order: Rib tips
River North$$
Lou Malnati's PizzeriaFamily-run since 1971, the most beloved name in Chicago deep dish.
Order: The Malnati Chicago Classic
South Loop$$
Manny's Cafeteria & DelicatessenThe country's oldest cafeteria-style Jewish deli since 1942.
Order: Hand-carved corned beef
Chinatown$$
MingHin CuisineThe biggest and best-known dim sum house in the Midwest.
Order: Har gow
Chicago$$
Nuevo LeonA nearly 50-year Pilsen family institution reopened in 2026.
Order: Carne asada
Lincoln Park$$
Pequod's PizzaCult favorite for its caramelized cheese halo ringing the pan crust.
Order: Caramelized-crust pan pizza
River North$$
Pizzeria UnoThe 1943 birthplace of Chicago deep dish.
Order: The original deep-dish
West Ridge$$
Sabri NihariMichelin Bib Gourmand Pakistani spot on Devon, famous for nihari.
Order: Sabri Nihari
Irving Park$$
Smoque BBQMichelin-recognized smokehouse with some of the best brisket outside Texas.
Order: Brisket
Chicago$$
StaropolskaIconic Logan Square destination for hearty old-country Polish plates.
Order: The Polish Platter
Norwood Park$
Superdawg Drive-InRetro carhop drive-in since 1948, a genuine Chicago time capsule.
Order: The Superdawg
Uptown$
Tank NoodleAnchor of Argyle Street's Asia on Argyle, a casual pho favorite.
Order: Pho tai
Fulton Market$$$
The PublicanA convivial beer-hall temple to pork, oysters, and craft brews.
Order: The famous ham
Magnificent Mile$$$
The Purple PigCheese, swine, and wine small plates a block off Michigan Ave.
Order: Milk-braised pork shoulder
Ashburn$$
Vito & Nick's PizzeriaSouth Side institution hailed as the GOAT of tavern-style thin crust; cash only.
Order: Cracker-thin sausage tavern pizza
Elmwood Park$
Johnnie's BeefCash-only suburban stand with a perpetual line and the gold-standard beef.
Order: Italian beef combo
River Grove$
Gene & Jude'sVoted the #1 hot dog in the country, fresh-cut fries piled on the dog.
Order: Depression dog with fries
Updated 2026-07-02. Measured venue distances appear only for checked restaurant pins; drive-time ranking comes after the broader precise-location pass.
Plan the logistics
Where to stay, and what to know.
Where to stay
Presidents Cup week spikes lodging around Medinah, Illinois. When rooms by the venue are gone or overpriced, the smarter play is to base an hour out and drive in along a scenic route - Roamward matches the stay to the drive. Lodging links below search stays around the event — the iOS beta adds the on-road companion.
Know before you go
Event week brings road closures, shuttle-only zones, and timed entry. We surface the passes, reservations, and closures that matter - and point you to the official source for tickets and schedules.
Presidents Cup →Play while you're in town
In Chicago suburbs, Illinois for the golf? See the public courses you can actually book nearby - and the designers behind them.
IL golf →Where to stay
Find a place to stay near Medinah, Illinois.
Hotels, cabins, and rentals close to the action — compare and book for your trip.
We may earn a commission from bookings made through this link — at no extra cost to you.
Event-trip guides
Roamward turns the trip around the event into the trip you remember.
Use the event and route guides on the web now, then open the external iOS beta for verified stops, shared trips, and poster-style trip cards.
Built for the shotgun seat: games, check-ins, and the next great stop — while the driver drives.
Build a trip around an event like this.
Save catalog-backed stops to My Trips on the web now. The iOS beta is testing the on-road companion: verified check-ins, badges, shared trips, and your growing map of America.