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Road trips · Illinois
Illinois road trips & hidden gems.
Illinois is Chicago’s skyline and lakefront set against downstate prairie, Route 66’s birthplace, and the sandstone canyons of Starved Rock. Summer and fall are prime; the city shines year-round. Big shoulders, big-hearted.
Happening in Illinois
Lollapalooza 2026
Barely two dozen marquee events hit the whole country in a year — and Illinois has one this July. Roamward builds the trip around it: the scenic route in, the detours worth a slack day, and when rooms sell out.
Best time to visitLate spring–fall
Don’t missThe Chicago lakefront on a clear day
Gem Hunt nominees10 candidates
Hikes10 curated
Scenic drives4
Worth-the-detour corridors
Drives through Illinois
Ranked city-to-city drives that cross Illinois — each with honest +N min detours on the shelf.
Gem Hunt nominees
What locals say you shouldn’t miss.
Community-nominated candidates. Add yours and vote to help choose the first published finalists.
Cave-in-Rock State Park
A 55-foot-wide limestone cave yawning straight onto the Ohio River in far-southern Illinois, once a hideout for river pirates, with a little ferry still shuttling cars across to Kentucky.
Garden of the GodsSandstone cliffs and balanced formations like Camel Rock crowning the Shawnee National Forest in southern Illinois — the quarter-mile Observation Trail has the best long views in the Midwest.
Mississippi Palisades State ParkLimestone bluffs tower 250-plus feet over the Mississippi near Savanna in Illinois' hilly northwest corner, with sweeping river overlooks in driftless country that looks nothing like flat Illinois.
Cozy Dog Drive InThe Springfield diner where the battered, deep-fried hot-dog-on-a-stick was perfected, and one of the last original eateries still cooking on Route 66 — a friendly, memorabilia-stuffed stop.
World's Largest Catsup BottleA 170-foot water tower shaped like a giant 1949 catsup bottle, looming over Collinsville near the St. Louis side — pure roadside Americana with a birthday festival every July.
Ferne Clyffe State ParkTucked in the Shawnee Hills near Goreville, this rugged park hides a 100-foot intermittent waterfall at the end of Big Rocky Hollow, plus shelter caves and narrow sandstone gorges — gloriously uncrowded.
Worth traveling for
Events that put Illinois on the calendar.
Explore by interest
Everything else worth a stop in Illinois.
Start with a few highlights, choose one interest, or explicitly open the full state guide.
Showing General guide and Scenic routes highlights. Choose a category or Show all for the full state guide.
Scenic drives
Scenic routes through Illinois.
Themed trails
Trails to follow in Illinois.
More worth the detour
The general guide to Illinois.
Museums, monuments, historic sites, and local-only stops from Roamward's shared place map.
Ambler's Texaco Gas Station
Restored 1933 gas station that pumped gas until 1999 — longest continuously operating station on Route 66; NRHP-listed; now Dwight's Route 66 visitor center.
Anderson Japanese GardensThe garden combines streams, waterfalls, winding paths, and koi ponds in a landscape designed with Hoichi Kurisu. The pond-strolling garden, bridges, and carefully placed stonework make this a focused one-to-two-hour walking stop.
Ariston CafeRoute 66 diner dating to 1935 (founded 1924 in Carlinville); billed as the longest continuously operating restaurant on the route, NRHP-listed 2006.
Ballard Nature CenterSix miles of trails cross restored tallgrass prairie, oak-hickory woodland, streams, wetlands, and ponds, with a wetland boardwalk and accessible observation deck. Trails remain open dawn to dusk beyond visitor-center hours.
Big Things Small TownA walkable downtown collection includes the world's largest wind chime, rocking chair, mailbox, teeter-totter, and many other oversized objects. Most outdoor pieces are free and viewable around the clock, but businesses keep their own hours.
Bunyon Giant19-foot fiberglass Muffler Man holding an oversized hot dog; built in the 1960s, relocated to Atlanta in 2003.
Boots on
Best hikes in Illinois.
From family-easy to bucket-list — trails worth the detour, great for the RV & camping crew.
Apple River Canyon
limestone bluffs in Illinois’s driftless northwest
Ferne Clyffea box canyon and seasonal waterfall in southern Illinois
Garden of the Gods (IL)sandstone cliffs over the Shawnee forest
Giant City Nature Trailsandstone "streets" in the Shawnee forest
Little Grand Canyon (IL)a box canyon with seasonal falls
Matthiessen (Dells)a streamcut canyon beside Starved Rock
Raise a glass
Breweries, distilleries & wineries in Illinois.
The trip-worthy taprooms, distilleries, and wine country.
Goose Island Beer Co
the Chicago original behind Bourbon County Stout and 312 Wheat.
Half Acre Beer Coa North Side favorite known for Daisy Cutter pale ale.
Koval DistilleryChicago’s first distillery since Prohibition, organic grain-to-bottle.
Maplewood Brewinga Logan Square brewery-and-distillery (Son of Juice IPA).
Off Color Brewinga playful brewery reviving old and odd beer styles.
Pipeworks Brewingan inventive, art-covered brewery with a deep, ever-rotating lineup.
Where to eat
Road-trip dining in Illinois.
Restaurants, diners, and food halls that fit the drive — curated by town, not scraped from a phone book.
Al's Beef
Original Little Italy stand since 1938 serving the archetypal dripping Italian beef sandwich, dunked and loaded with giardiniera.
Al's Italian BeefThe Taylor Street original that helped invent the Chicago Italian beef. (Little Italy)
AlineaOne of America's most celebrated tasting-menu destinations. (Lincoln Park)
Au ChevalThe diner-style spot behind what's called the best cheeseburger in America. (West Loop)
AvecCozy West Loop wine bar serving Mediterranean-leaning small plates at communal seating, an enduring Chicago dining pioneer.
Bavette'sSultry River North steakhouse with a speakeasy vibe and 1920s jazz, serving impeccably cooked steaks and a famous roasted bone marrow.
Sand & surf
Best beaches in Illinois.
Family sand, surf breaks, wild shores — find your vibe.
Tee it up
Public golf you can book in Illinois.
Wheaton · $$$
Galena · $$$
Chicago · $$$
Grayslake · $$$
Glenview · $$$
Beacons
Lighthouses in Illinois.
Take me out
MLB ballparks in Illinois.
Plan the Illinois trip
Get the scenic route, the stops, and the timing.
Explore and save the trip on the web now. Join the iOS beta list for verified check-ins, shared trips, badges, and your growing map.
Where to stay
Find a place to stay near Illinois.
Hotels, cabins, and rentals close to the action — compare and book for your trip.
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