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Every stop worth the detour.
The crowd-favorite places that make a drive worth remembering — waterfalls, beaches, hot springs, hikes, scenic landmarks, dining, breweries, ballparks and more. Browse by category or state, find what's near you, and plan the detour with Roamward.
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99 stopsIL
Sources: 99 Roamward guides · live place map
LighthousesChicago Harbor LightIL · Great Lakesthe classic offshore light off Navy Pier with the city skyline behind itView guide →HikesApple River CanyonIL · Moderatelimestone bluffs in Illinois’s driftless northwestView guide →MLB ballparksRate FieldIL · Modernthe South Side park (formerly Comiskey/Guaranteed Rate) — exploding scoreboard, great sausageView guide →MLB ballparksWrigley FieldIL · Classicthe ivy, the hand-turned marquee, rooftops across the street — a pilgrimage even for non-fansView guide →DiningAl's BeefIL · DeliOriginal Little Italy stand since 1938 serving the archetypal dripping Italian beef sandwich, dunked and loaded with giardiniera. Order: Italian beef dipped witView guide →DiningAl's Italian BeefIL · AmericanThe Taylor Street original that helped invent the Chicago Italian beef. (Little Italy)View guide →GolfCantignyIL · publicA polished 27-hole public course on a former estate.View guide →DiningAlineaIL · Fine DiningOne of America's most celebrated tasting-menu destinations. (Lincoln Park)View guide →Breweries & distilleriesGoose Island Beer CoIL · Brewerythe Chicago original behind Bourbon County Stout and 312 WheatView guide →Breweries & distilleriesHalf Acre Beer CoIL · Brewerya North Side favorite known for Daisy Cutter pale aleView guide →BeachesIllinois Beach State ParkIL · Wildthe only remaining natural dune shoreline in IllinoisView guide →GolfCog Hill (No. 2)IL · publicA more playable course at the famous 72-hole complex.View guide →GolfCog Hill (No. 4 Dubsdread)IL · publicA brutal public course that hosted the PGA Tour for years.View guide →Breweries & distilleriesKoval DistilleryIL · DistilleryChicago’s first distillery since Prohibition, organic grain-to-bottleView guide →Breweries & distilleriesMaplewood BrewingIL · Brewerya Logan Square brewery-and-distillery (Son of Juice IPA)View guide →GolfEagle Ridge (The General)IL · resortA dramatic course in the hills of northwest Illinois.View guide →HikesFerne ClyffeIL · Easya box canyon and seasonal waterfall in southern IllinoisView guide →Breweries & distilleriesOff Color BrewingIL · Brewerya playful brewery reviving old and odd beer stylesView guide →BeachesNorth Avenue BeachIL · FamilyChicago’s busiest lakefront beach with a skyline backdropView guide →HikesGarden of the Gods (IL)IL · Easysandstone cliffs over the Shawnee forestView guide →BeachesOak Street BeachIL · Scenica curving downtown Chicago beach beneath the skylineView guide →HikesGiant City Nature TrailIL · Easysandstone "streets" in the Shawnee forestView guide →Breweries & distilleriesPipeworks BrewingIL · Breweryan inventive, art-covered brewery with a deep, ever-rotating lineupView guide →DiningAu ChevalIL · New AmericanThe diner-style spot behind what's called the best cheeseburger in America. (West Loop)View guide →Breweries & distilleriesRevolution BrewingIL · BreweryIllinois’s largest independent brewery, with a lively Logan Square brewpubView guide →DiningAvecIL · MediterraneanCozy West Loop wine bar serving Mediterranean-leaning small plates at communal seating, an enduring Chicago dining pioneer. Order: Chorizo-stuffed dates.View guide →GolfGeorge Dunne NationalIL · publicA strong, affordable forest-preserve course.View guide →GolfHarborside InternationalIL · publicTwo links courses on reclaimed land near the city.View guide →DiningBavette'sIL · SteakhouseSultry River North steakhouse with a speakeasy vibe and 1920s jazz, serving impeccably cooked steaks and a famous roasted bone marrow. Order: Dry-aged ribeye.View guide →DiningBavette's Bar & BoeufIL · SteakhouseIntimate 1920s-speakeasy-styled steakhouse with a devoted following. (River North)View guide →HikesLittle Grand Canyon (IL)IL · Moderatea box canyon with seasonal fallsView guide →Breweries & distilleriesTwo Brothers BrewingIL · Brewerya western-suburbs roundhouse brewery, coffee roaster, and taproomView guide →HikesMatthiessen (Dells)IL · Easya streamcut canyon beside Starved RockView guide →HikesMississippi PalisadesIL · Moderatecliff-top views over the Mississippi RiverView guide →DiningBig JonesIL · SouthernAndersonville restaurant devoted to heirloom Southern and Creole cooking with a deep focus on historic recipes and provenance. Order: Buttermilk fried chicken.View guide →HikesPere Marquette (Goat Cliff)IL · Moderatebluffs over the Illinois River near its mouthView guide →GolfPine MeadowIL · publicA well-regarded north-suburban public course.View guide →GolfRich Harvest FarmsIL · privateJerry Rich's personal masterpiece outside Chicago has quietly hosted a Solheim Cup and an NCAA final, yet almost no one ever plays it. The definition of rare.View guide →HikesRim RockIL · Easya clifftop nature loop in the ShawneeView guide →HikesStarved Rock (Waterfall Canyons)IL · Moderatecanyon waterfalls along the Illinois RiverView guide →GolfStonewall OrchardIL · publicA Hurdzan-design and frequent US Open qualifier.View guide →DiningCalumet FisheriesIL · SeafoodFamily smokehouse near the East Side smoking all its own seafood over natural wood, a James Beard America's Classic with no seating. Order: Garlic-smoked salmonView guide →GolfThe Glen ClubIL · publicA Tom Fazio course on a former naval air base.View guide →DiningCarnitas UruapanIL · MexicanPilsen institution since 1975 slow-cooking Michoacan-style carnitas and the best chicharrones in the city in a bustling counter setting. Order: Carnitas by the View guide →GolfThunderHawkIL · publicA Robert Trent Jones Jr. forest-preserve course.View guide →DiningCho Sun OkIL · KoreanLongstanding Lincoln Square Korean spot delivering Seoul-style tabletop barbecue and bubbling stews in a no-frills setting. Order: Bulgogi.View guide →DiningCoalfireIL · PizzaWest Town pioneer of coal-fired pizza with a blistered, charred crust topped with fennel sausage and whipped ricotta. Order: Fennel sausage pizza.View guide →DiningCozy Dog Drive InIL · AmericanA Route 66 original in Springfield, Illinois, built around the battered hot dog on a stick that became a road-food icon.View guide →DiningDemeraIL · EthiopianChicago's top-rated Ethiopian, communal platters and honey wine. (Uptown)View guide →DiningEverIL · Fine DiningCurtis Duffy's two-Michelin-star West Loop restaurant delivers meticulous contemporary American cuisine with polished, warm service. Order: Tasting menu.View guide →DiningFried Green TomatoesIL · ItalianSeasonal modern Italian-American cuisine served in a cozy exposed-brick-and-stone setting with locally sourced ingredients, ideal for a special river-town occasView guide →DiningFritz and FritesIL · GermanCharming European bistro fusing German and French cuisines with dishes like schnitzel, steak frites, and garlic roasted chicken. Order: Wiener schnitzel.View guide →DiningFrontera GrillIL · MexicanRick Bayless's lively River North room offers vibrant, thoughtfully sourced regional Mexican cooking in a more casual companion to Topolobampo. Order: Carne asaView guide →DiningGene & GeorgettiIL · SteakhouseOld-school 1941 steakhouse pairing aged steaks with Italian classics. (River North)View guide →DiningGene & Jude'sIL · AmericanVoted the #1 hot dog in the country, fresh-cut fries piled on the dog. (River Grove)View guide →DiningGibsonsIL · SteakhouseIconic Gold Coast steakhouse where regulars, tourists, and celebrities gather over big prime steaks and famously attentive service. Order: Bone-in ribeye.View guide →DiningGibsons Bar & SteakhouseIL · SteakhouseA Chicago rite of passage for martinis, big steaks, and people-watching. (Gold Coast)View guide →DiningGirl & the GoatIL · New AmericanStephanie Izard's boisterous flagship of bold small plates. (Fulton Market)View guide →DiningGreek IslandsIL · GreekA white-tablecloth Greektown staple since 1971.View guide →DiningHigh Five RamenIL · RamenIntimate subterranean ramen counter beneath Green Street Smoked Meats with just fifteen seats and a fiery signature bowl. Order: Spicy High Five ramen.View guide →
Category guides
Go deeper, interest by interest.
99 stops across 19 state-by-state guide collections.
Hikes500+ trails in every state, easy to epic545 stops →Waterfalls300+ falls, roadside to bucket-list303 stops →BeachesFamily sand, surf breaks, and wild shores299 stops →Hot springsLuxe resorts to wild backcountry soaks90 stops →Mountain bikingTrail systems, bike parks, and gravel76 stops →CyclingScenic rides, climbs, and rail-trails50 stops →Ski & snowboardBig-mountain steeps to family hills86 stops →DiningGreat meals near routes and gateway towns3,924 stops →Breweries & distilleriesTrip-worthy taprooms and still houses267 stops →GolfPublic courses you can actually book753 stops →National parksAll 63, guided by season and top sights63 stops →Hidden gemsVote favorites into the Roamward map19 stops →MLB ballparksAll 30 MLB parks as a road-trip quest30 stops →LighthousesCoast-to-coast beacons worth the drive60 stops →EventsPlan the trip around the moment31 stops →Wild landsForests, wilderness, and monuments beyond the parks74 stops →CampingEpic campgrounds by where you want to wake up63 stops →Scenic landmarksIconic overlooks, canyons, dunes, and formations57 stops →Roadside AmericanaGiant statues, folk art, oddities, and vintage neon23 stops →
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