Illinois is Chicago and then 90 percent of the state that nobody plans a holiday around. That is a fair summary of visitor numbers and an unfair summary of the place. Chicago is one of the great cities of the world for architecture and museums, and it earns four days on its own. Beyond it there is the original Route 66, Frank Lloyd Wright’s home turf, Abraham Lincoln’s Springfield, and a stretch of the Mississippi that looks nothing like the popular image of the Midwest.
The practical question for most visitors is whether anything outside Chicago justifies a car. For a first trip, probably not. For a second, Springfield and the river towns make an easy loop.
The quick answer
How long: four days for Chicago. Six or seven to add Springfield and the Illinois stretch of Route 66.
Chicago is a walking and transit city. Do not hire a car for it. Parking downtown runs $40 to $60 a day.
Best months: May, June, September and early October. Chicago in July is humid and crowded, and in January it is genuinely severe.
The airport train matters. The Blue Line from O’Hare to the Loop takes about 45 minutes for a few dollars and beats a taxi in traffic.
Book the architecture river cruise ahead in summer. It is the single best thing to do in the city and it sells out.
Daily budget: roughly $170 to $250 per person mid-range in Chicago, considerably less outside it.
Chicago
Our Chicago travel guide covers the city properly. The short version of why it deserves the time:
The architecture. The modern skyscraper was effectively invented here after the 1871 fire, and the result is a downtown that reads as a timeline of the form. The river cruise run by the Chicago Architecture Center is the best 90 minutes available in any American city.
The museums. The Art Institute is one of the strongest collections in the country, particularly for Impressionism and American painting. The Field Museum, the Museum of Science and Industry and the Adler Planetarium make up the rest of a serious museum city.
The lakefront. Lake Michigan gives Chicago 42 kilometres of continuous public shoreline with a path along most of it, and actual sand beaches within the city limits. In summer it functions as a coast.
The food. Deep dish is the tourist dish and thin crust tavern-style is what locals actually eat. Beyond pizza there is an Italian beef sandwich worth understanding, a strong Mexican food scene in Pilsen and Little Village, and a fine dining tier that punches far above the city’s reputation.
Neighbourhoods. Wicker Park and Logan Square for bars and independent shops, Pilsen for murals and Mexican food, Hyde Park for the university and the Obama Presidential Center, Andersonville for a quieter evening.
Beyond Chicago
Oak Park, 25 minutes out on the Green Line, holds the largest concentration of Frank Lloyd Wright buildings anywhere, including his home and studio. It is the easiest half day trip from the city and needs no car.
Springfield, three and a half hours south west, is where Abraham Lincoln lived for a quarter of a century. The Abraham Lincoln Presidential Library and Museum, his only owned home, his law office and his tomb are all within a compact area. Worth an overnight rather than a day trip from Chicago.
Route 66 begins in downtown Chicago and runs 480 kilometres across the state to St Louis. The Illinois stretch has more surviving original road and more preserved roadside architecture than most sections, including the Gemini Giant at Wilmington, the Cozy Dog Drive In at Springfield and a chain of small towns that exist because of it. 2026 marks the centenary of the road’s establishment in 1926, and commemorative events are running through the year.
Galena, in the far north west, is a preserved 19th century river town in hill country that geologists call the Driftless Area, missed by the glaciers that flattened everything around it. Three hours from Chicago and the best weekend escape in the state.
Starved Rock State Park, 90 minutes south west, has 18 canyons with waterfalls after rain or during the spring thaw. It is the most-visited state park in Illinois and busy at weekends.
Shawnee National Forest, at the southern tip, is closer to Kentucky than to Chicago in both distance and character, with sandstone formations at the Garden of the Gods. A six-hour drive from the city, so a destination in itself rather than an add-on.
When to go
May and June are the sweet spot: warm, green, the lakefront waking up, festival season beginning.
September and early October are the other one, with the humidity gone and the light better than any other time of year.
July and August are hot, humid and full. This is festival season, including Lollapalooza and the Air and Water Show, so the city is at its liveliest and its most expensive.
November to March is cold, and January and February are severe. Wind off the lake makes the effective temperature considerably lower than the number. The trade-off is genuinely cheap hotel rates, a strong indoor culture of museums, theatre and comedy, and a city that does not feel touristy at all.
Spring is unreliable. April can deliver both snow and 25 degrees in the same week.
What it costs
Accommodation: $170 to $280 a night mid-range in the Loop or River North, $120 to $180 in Wicker Park or Lincoln Park, and under $120 across most of the rest of the state. Chicago hotel taxes are among the highest in the country at around 17 percent.
Transit: a single CTA ride is a few dollars, and a multi-day pass covering trains and buses is good value. The system runs 24 hours on two lines.
Eating: $15 to $22 for a casual lunch, $35 to $65 per person for dinner with a drink. Chicago restaurants often add a service charge of 3 to 5 percent to cover employee healthcare, disclosed at the foot of the menu and separate from the tip.
Museums: $25 to $40 each. The city passes bundle several and pay off from three attractions upwards.
Car hire is only worth it if you are leaving the city. $45 to $70 a day plus parking, which is the expensive part.
A route that works
Four days, city only. Two days downtown for architecture and the Art Institute, one for the lakefront and a neighbourhood, one for Oak Park and a museum.
Seven days, city and state. Four days Chicago without a car, then hire one and drive Route 66 south to Springfield for two nights, returning via Starved Rock.
A long weekend from elsewhere. Chicago is well connected and works as a three-night city break. O’Hare and Midway between them reach almost everywhere.
Practical notes
The wind is not the reason for the nickname, but it is real, and lakefront temperatures in winter are meaningfully lower than the forecast suggests. Layers, and a hat you would not otherwise wear.
The L is elevated in the centre and underground elsewhere. Both O’Hare and Midway are on the network, which is unusual for an American city and worth using.
Chicago’s reputation for crime is disproportionate to what a visitor will experience in the areas they are likely to be in. Standard city awareness applies, particularly late at night on transit.
Tipping is 18 to 20 percent in restaurants, and check whether a service charge has already been added.
Route 66 signage is inconsistent. Download a route map before you drive it, because the historic alignment splits and rejoins the interstate repeatedly.
Frequently asked questions
How many days do you need in Chicago?
Four is right for a first visit: two downtown for the architecture and the Art Institute, one for the lakefront and a neighbourhood, and one for Oak Park or a second museum. Three works if you skip the neighbourhoods.
What is the best time to visit Illinois?
May, June, September and early October. Summer is humid, busy and full of festivals, while January and February are severely cold, though hotel rates fall accordingly and the museums and theatre are at their best then.
Do I need a car in Chicago?
No, and it is a liability. The city is walkable, the L reaches both airports, and downtown parking runs $40 to $60 a day. Hire a car only for the day you leave the city for Springfield, Galena or Route 66.
Is anything in Illinois worth seeing outside Chicago?
Yes, though not on a first trip. Springfield for Lincoln, Galena for a preserved 19th century river town, Starved Rock for canyons and waterfalls, and the Illinois stretch of Route 66, which has more surviving original road than most states.
Deep dish or thin crust in Chicago?
Try deep dish once because you are there, then eat tavern-style thin crust, which is what people in Chicago actually order. The Italian beef sandwich is the other local dish worth working out.
How do I get from O’Hare to downtown Chicago?
The Blue Line train, which takes around 45 minutes to the Loop for a few dollars and runs 24 hours. In traffic it beats a taxi on both time and cost. Midway is on the Orange Line, about 30 minutes out.
Is Route 66 worth driving in Illinois?
The Illinois section is one of the better preserved, running 480 kilometres from downtown Chicago to St Louis with a lot of original alignment and roadside architecture intact. 2026 is the centenary of the road, with events running through the year.
How cold does Chicago get in winter?
Cold enough to plan around. January and February regularly sit below freezing all day, and wind off Lake Michigan makes it feel considerably worse. The compensation is cheap hotel rates and a city that belongs to its residents again.
How much does a trip to Chicago cost?
Roughly $170 to $250 per person per day mid-range, with hotel tax near 17 percent on top of the room rate. Outside Chicago, Illinois is one of the cheaper states in the country for accommodation and food.
Plan the rest of your Illinois trip
Chicago. The city guide, the architecture boat tour, where to stay, the museums, Millennium Park and the lakefront and the food guide.
The rest of the state. Route 66, Springfield and the Lincoln sites and Starved Rock and Galena.
Planning. The best time to visit and Illinois on a budget.
