Illinois
5
Day Itinerary •
USA
Five days in Illinois gives you the full extraordinary breadth of the Prairie State, from the world-class architecture, food and culture of Chicago to the extraordinary canyon system of Starved Rock, the Route 66 heritage of the Mother Road across the Illinois heartland and the remarkable Cahokia Mounds, the most extraordinary pre-Columbian site north of Mexico. This route covers the complete Illinois experience. The extraordinary Art Institute and Millennium Park of Chicago, Willis Tower and the finest deep-dish pizza in America, the extraordinary Starved Rock and Matthiessen canyon waterfalls, the Route 66 roadside Americana of Springfield and Pontiac and the extraordinary Cahokia Mounds World Heritage Site.
Best Time To Visit
May to October for Chicago lakefront and canyon waterfalls
Getting There
Fly into O'Hare (ORD) or Midway (MDW)
Getting Around
CTA in Chicago. Rental car for days 3 to 5.
Budget Per Day
Approx $120 to $200 per person per day
Difficulity
Easy, mostly walking and transit
DAY 1
CHICAGO ARCHITECTURE
MORNING
CHICAGO ARCHITECTURE RIVERWALK AND THE MAGNIFICENT MILE
The Chicago Architecture Center river cruise is the most extraordinary architecture tour in America, its extraordinary 90-minute journey along the Chicago River giving close-range views of over 50 landmark buildings including the Willis Tower, Tribune Tower, Marina City and the Wrigley Building. The Chicago Riverwalk promenade itself is the most extraordinary urban waterway in the Midwest. The Magnificent Mile on Michigan Avenue is the finest retail and architectural street in Chicago. Cruise approx $48. Drive: 30 min CTA
MIDDAY
WILLIS TOWER SKYDECK AND THE LOOP ARCHITECTURE
The Willis Tower Skydeck at 1,353 feet gives the most extraordinary panoramic view of Chicago, its extraordinary glass-floored Ledge boxes extending beyond the building face giving the finest aerial perspective of the lakefront and the grid of the world's most extraordinary architectural city. The surrounding Loop contains Sullivan's Carson Pirie Scott building, Burnham and Root's Rookery Building and Mies van der Rohe's Federal Plaza in the finest concentration of architecture in America. Skydeck approx $30. Drive: 10 min walk
AFTERNOON
NAVY PIER AND THE LAKE MICHIGAN LAKEFRONT
Navy Pier is the most extraordinary lakefront attraction in Chicago, its 3,300-foot pier giving extraordinary views of the downtown skyline from Lake Michigan. The extraordinary 18-mile Lakefront Trail is the finest urban cycling and walking path in America. The Museum of Science and Industry in Hyde Park, the finest science museum in the country, is an extraordinary half-day. Chicago's lakefront beaches at Oak Street and North Avenue are extraordinary in summer. Navy Pier free.
💎 HIDDEN GEM
The extraordinary Newberry Library on Walton Street is the finest free research library and cultural institution in Chicago, its extraordinary collection of 1.5 million rare books and manuscripts open to the public in a magnificent 1893 Romanesque building. Free exhibitions, map collection extraordinary. The most extraordinary hidden cultural gem in Chicago.
🍽 WHERE TO EAT
Breakfast: Lou Mitchell's, The Loop The most legendary breakfast in Chicago since 1923. Extraordinary omelets, fresh donuts and malted milk. | Lunch: Portillo's, River North The finest Chicago-style hot dog and Italian beef in the city. An extraordinary institution since 1963. | Dinner: Lou Malnati's Pizzeria The most celebrated deep-dish pizza in Chicago. Extraordinary butter crust. Book ahead or expect a wait.
DAY 2
CHICAGO CULTURE
MORNING
ART INSTITUTE OF CHICAGO, THE FINEST ART MUSEUM IN THE MIDWEST
The Art Institute of Chicago is the most extraordinary art museum in the Midwest, its collection of 300,000 works including the finest Impressionist collection in America outside New York. Seurat's A Sunday on La Grande Jatte, Grant Wood's American Gothic and Edward Hopper's Nighthawks are all extraordinary. The Modern Wing by Renzo Piano is the finest museum extension in America. The extraordinary Thorne Miniature Rooms are the finest hidden gallery in any American museum. Entry approx $25. Drive: 15 min walk
MIDDAY
MILLENNIUM PARK, CLOUD GATE AND PRITZKER PAVILION
Millennium Park is the most extraordinary free urban park in Chicago, its extraordinary 24.5 acres containing Anish Kapoor's Cloud Gate, the most visited public sculpture in America, Frank Gehry's extraordinary Jay Pritzker Pavilion bandshell with its remarkable trellis of speakers extending across the Great Lawn, and Jaume Plensa's Crown Fountain video sculptures. The park hosts free concerts all summer. The adjacent Chicago Cultural Center with its Tiffany domes is free. Drive: 5 min walk
AFTERNOON
WICKER PARK, THE 606 TRAIL AND THE WEST LOOP
The 606 elevated trail gives an extraordinary 2.7-mile walk above the rooftops of Wicker Park, Bucktown and Logan Square along a converted railway, Chicago's finest answer to the High Line. Wicker Park below is the most extraordinary creative neighborhood in Chicago. The West Loop's Randolph Street Restaurant Row is the finest dining street in the Midwest. The Fulton Market cold storage district converted into tech offices and restaurants is extraordinary. The 606 completely free.
💎 HIDDEN GEM
The extraordinary Chicago Cultural Center at 78 East Washington is the finest free building in Chicago, its extraordinary 1897 interior with two stunning Tiffany glass domes giving the most extraordinary architectural experience in the city at no cost. The Preston Bradley Hall dome is 38 feet across. Free. Open daily. The finest hidden architectural gem in Chicago.
🍽 WHERE TO EAT
Breakfast: Dove's | Lunch: Au Cheval, West Loop The most celebrated burger in Chicago. Queue from 11am. Extraordinary smash burger. | Dinner: Alinea, Lincoln Park The most extraordinary restaurant in America. Three Michelin stars. Book months ahead.
DAY 3
STARVED ROCK
MORNING
STARVED ROCK STATE PARK CANYON TRAIL
Starved Rock State Park is the most extraordinary state park in Illinois, its extraordinary 18 canyons carved through St. Peter sandstone along the Illinois River giving a landscape entirely unexpected in the Midwest. The French Canyon with its extraordinary 80-foot waterfall in spring and the Starved Rock bluff overlooking the Illinois River are the finest. The 13-mile main trail system connects all the major canyons. Entry free. Drive: 1.5 hr drive
MIDDAY
MATTHIESSEN STATE PARK DELLS CANYONS
Matthiessen State Park adjacent to Starved Rock is the most extraordinary hidden canyon park in Illinois, its extraordinary two-tiered Dells Area with its upper and lower canyons connected by a 45-foot waterfall giving a canyon experience far less visited than Starved Rock but equally extraordinary. The Giant's Bathtub glacial pool and Cascade Falls are unmissable. The extraordinary Vermilion River below the park gives the finest kayaking in north-central Illinois. Entry free. Drive: 15 min drive
AFTERNOON
ILLINOIS RIVER BALD EAGLE VIEWING
The Illinois River valley below Starved Rock is the most extraordinary bald eagle watching location in the central United States from January to March, its extraordinary winter concentration of hundreds of eagles drawn by open water below the dams giving the finest eagle viewing in the Midwest. The Starved Rock Dam and the Illinois Waterway Visitor Center give the finest eagle viewpoints. The extraordinary Utica town with its historic taverns and the Heritage Canyon living history site are outstanding. Free.
💎 HIDDEN GEM
The extraordinary Plum Island Canyon in Matthiessen State Park is the finest hidden canyon in Illinois, its extraordinary narrow sandstone slot accessible by a short trail from the lower dells that almost no visitors find. The extraordinary fern-draped walls and the seasonal waterfall are extraordinary. Free. The finest hidden gem in Starved Rock country.
🍽 WHERE TO EAT
Breakfast: Starved Rock Lodge dining room Extraordinary lodge breakfast with Illinois River valley views before the canyon hike. | Lunch: Tavern on the Green, Utica Outstanding Illinois River town pub lunch. Local craft beer and Illinois beef burger. | Dinner: Grizzly Jack's Grand Bear Resort Outstanding lodge dining near Starved Rock. Local Illinois cuisine and craft beer.
DAY 4
ROUTE 66 ILLINOIS
MORNING
ROUTE 66 ILLINOIS HERITAGE, PONTIAC TO SPRINGFIELD
The Illinois section of Route 66 is the most extraordinary stretch of the Mother Road, its extraordinary 300 miles from Chicago to the Missouri border preserving the finest concentration of original roadside Americana in America. The Route 66 Hall of Fame Museum in Pontiac is the finest Route 66 museum in existence. The extraordinary Gemini Giant fiberglass muffler man at Wilmington and the Sundown Drive-In at Litchfield are the finest roadside attractions in Illinois. Museum free. Drive: 1.5 hr drive
MIDDAY
SPRINGFIELD, ABRAHAM LINCOLN'S HOME CITY
Springfield is the most extraordinary Lincoln heritage city in America, its extraordinary Abraham Lincoln Presidential Library and Museum the finest presidential museum in the United States. Lincoln's Home National Historic Site preserves the only home Lincoln ever owned. The extraordinary Lincoln Tomb in Oak Ridge Cemetery is the most visited presidential grave in America. The Old State Capitol where Lincoln delivered his House Divided speech is extraordinary. Library entry approx $15. Drive: 1 hr drive
AFTERNOON
COZY DOG DRIVE-IN AND ROUTE 66 SPRINGFIELD
The Cozy Dog Drive-In on South Sixth Street in Springfield is the most extraordinary Route 66 institution in Illinois, its extraordinary claim as the birthplace of the corn dog in 1946 giving it legendary status among Route 66 travelers. The walls are covered with Route 66 memorabilia and every table has a story. The extraordinary Shea's Gas Station Museum nearby preserves the finest collection of Route 66 petroliana in the state. Cozy Dog approx $5.
💎 HIDDEN GEM
The extraordinary Funk's Grove Pure Maple Sirup operation near Shirley on Route 66 is the finest hidden roadside stop in Illinois, its extraordinary family maple syrup operation producing the finest pure maple sirup in the Midwest since 1891. The name is spelled Sirup by family tradition. Free to visit, sirup from approx $12. The most extraordinary hidden gem on Route 66 Illinois.
🍽 WHERE TO EAT
Breakfast: Maid-Rite, Springfield The most legendary loose meat sandwich in Illinois. An extraordinary Route 66 institution since 1926. | Lunch: Obed and Isaac's Microbrewery, Springfield Outstanding Lincoln country lunch. Illinois craft beer and local beef burger in a historic building. | Dinner: Incredibly Delicious, Springfield The finest restaurant in Springfield. Extraordinary local Illinois produce and outstanding wine list.
DAY 5
CAHOKIA AND THE MISSISSIPPI
MORNING
CAHOKIA MOUNDS, THE MOST EXTRAORDINARY PRE-COLUMBIAN SITE IN NORTH AMERICA
Cahokia Mounds State Historic Site and UNESCO World Heritage Site is the most extraordinary pre-Columbian site north of Mexico, its extraordinary 80 surviving earthen mounds constructed by the Mississippian culture between 900 and 1300 AD at the largest pre-Columbian settlement north of Mexico with a population of up to 20,000 people. Monks Mound, the largest prehistoric earthwork in North America at 100 feet tall and 14 acres at the base, is extraordinary. Entry free. Drive: 1 hr drive
MIDDAY
GATEWAY ARCH, ST LOUIS, MISSOURI
The Gateway Arch in St Louis just across the Mississippi is the most extraordinary monument in the American Midwest, its extraordinary 630-foot stainless steel catenary arch designed by Eero Saarinen the tallest man-made monument in the United States. The tram ride to the top gives the most extraordinary view of the Mississippi River and the Illinois-Missouri border. The Museum at the Gateway Arch below gives the finest history of westward expansion in America. Tram entry approx $16. Drive: 20 min drive
AFTERNOON
THE GREAT RIVER ROAD AND THE MISSISSIPPI BLUFFS
The Great River Road along the Mississippi bluffs north of St Louis through the Illinois towns of Alton and Grafton is the most extraordinary river drive in Illinois, its extraordinary limestone bluffs above the confluence of the Missouri and Mississippi Rivers giving the finest view of the great river junction in America. The extraordinary Pere Marquette State Park above Grafton gives the finest overlook. The Brussels ferry across the Illinois River is the most extraordinary free river crossing in the state.
💎 HIDDEN GEM
The extraordinary Woodhenge at Cahokia Mounds is the finest hidden feature of the site, its extraordinary reconstruction of the original timber circle used by the Mississippians to mark the solstices and equinoxes giving the most extraordinary astronomical alignment experience in North America at sunrise on the equinox. Free with site entry. Almost entirely unknown.
🍽 WHERE TO EAT
Breakfast: Old Bakery Beer Company, Alton The finest breakfast near Cahokia Mounds. Outstanding local beer and extraordinary eggs in a 1866 bakery. | Lunch: Bigelo's Blue Ribbon BBQ, Grafton Outstanding Mississippi River BBQ at the finest riverside restaurant on the Great River Road. | Dinner: Franco, St Louis The finest French restaurant in St Louis. Extraordinary local Missouri and Illinois produce.
Where To Stay
Chicago, Nights 1 to 2 The Langham or Hotel EMC2 River North. Approx $150 to $300 per night. Starved Rock or Ottawa, Night 3 Starved Rock Lodge or Holiday Inn Ottawa. Approx $100 to $160 per night. Springfield or Cahokia, Nights 4 to 5 Inn at 835 Springfield or Drury Inn Fairview Heights. Approx $100 to $170.
Top Tips
1. Chicago Architecture Center river cruise is the finest architecture tour in America. Book in advance in summer.
2. Cahokia Mounds is the most extraordinary pre-Columbian site in North America. Free and largely unknown outside Illinois.
3. Route 66 in Illinois: the Gemini Giant fiberglass figure at Wilmington is the finest roadside attraction in the state.
4. Springfield's Abraham Lincoln Presidential Library is the finest presidential museum in America. Entry approx $15.
5. Starved Rock: French Canyon and Ottawa Canyon have waterfalls spring through early summer. Go early to park.
6. The Cozy Dog Drive-In in Springfield is the birthplace of the corn dog. A Route 66 institution since 1946.
Total Budget
$120 to $200/day