Chicago, IL Road Trips
Chicago, IL serves as a quiet starting point in the Midwest, connecting drivers to 60 outbound routes across the area. The route mix is balanced, with options ranging from 59-mile quick runs to 322-mile cross-state drives. Routes from Chicago, IL spread mainly west and south, covering a wide geographic range.
Photo: Otoniel Alvarado
Trip Routes
120
Longest Drive
360 mi
Rosiclare, IL
Quickest Drive
1h 13m
Kankakee, IL
Plan Around Chicago, IL
Popular Incoming Routes
Useful if Chicago, IL is the arrival point and you want the strongest routes into the city first.
Continue From Chicago, IL
Good next legs if this city is only one stop in a longer road trip.
Trips from Chicago, IL
Chicago, IL to Crainville, IL
Chicago, IL to Burton, IL
Chicago, IL to Johnston City, IL
Chicago, IL to Quincy, IL
Chicago, IL to Adams, IL
Chicago, IL to Sesser, IL
Chicago, IL to Norris City, IL
Chicago, IL to Alorton, IL
Chicago, IL to Saint Rose, IL
Chicago, IL to Barry, IL
Chicago, IL to Rosewood Heights, IL
Chicago, IL to Cincinnati, IL
Chicago, IL to Bethalto, IL
Chicago, IL to City of Greenville, IL
Chicago, IL to Vernon, IL
Chicago, IL to La Harpe, IL
Chicago, IL to Barr, IL
Chicago, IL to Markham, IL
Driving from Chicago, IL
The typical drive from Chicago, IL covers about 178 miles and takes around 3h 32m. There is a healthy spread of short hops, medium drives, and longer road trips to pick from. The longest mapped route runs 322 miles (6h 4m), while the shortest is just 59 miles.
Popular Destinations
Top road trip destinations from Chicago, IL are Crainville, IL (321.6 mi, 5h 59m), Burton, IL (313.7 mi, 5h 57m), Johnston City, IL (311.4 mi, 5h 46m), Zeigler, IL (310.7 mi, 5h 48m), and Quincy, IL (309.6 mi, 5h 53m). Most destinations stay within the same state, perfect for exploring the local region thoroughly.
Planning & Costs
Regular gas in IL currently averages around $3.77 per gallon. For the typical 178-mile trip from Chicago, IL, budget about $26 in fuel one way, assuming 25 MPG. Longer hauls and premium fuel will cost proportionally more.
Most routes head west — leaving in the morning keeps the sun behind you for a more comfortable drive. Most trips take a half-day, so a morning start gets you there in time for lunch or an afternoon of exploring.
Frequently Asked Questions
There are 60 mapped routes leaving Chicago, IL and 60 routes heading into Chicago, IL, covering 120 total connections. Distances range from 59 to 322 miles.
The longest mapped route from Chicago, IL covers 322 miles and takes approximately 6h 4m. Shorter options start at just 59 miles.
The average route from Chicago, IL runs about 178 miles with a drive time of roughly 3h 32m. This includes both short day trips and longer multi-day drives.
At current gas prices (about $3.77/gallon for regular), the average 178-mile trip from Chicago, IL costs roughly $26 in fuel one way, based on 25 MPG. Your actual cost depends on your vehicle's efficiency.
The most popular road trip destinations from Chicago, IL include Crainville, IL, Burton, IL, Johnston City, IL and Zeigler, IL. Each route page has detailed drive times, fuel estimates, stop suggestions, and turn-by-turn directions.
Chicago, IL by the Numbers
Recent demographic snapshot from the US Census Bureau's American Community Survey.
Population
2,707,648
Median Income
$75,134
Median Home Value
$315,200
Median Age
35.7
Source: US Census Bureau ACS 5-year (public domain). See our methodology for details.
Chicago, IL at a Glance
Elevation
587 ft
Area
234 mi²
Sister Cities
Notable People from Chicago, IL
A sampling of people born in Chicago, IL.
Walt Disney
1901–1966
American animator, producer, director, screenwriter, voice actor and entrepreneur, founder of The Walt Disney Company (1901–1966)
Leo XIV
1955
267th Pope of the Catholic Church (2025–)
Robin Williams
1951–2014
American actor and comedian (1951–2014)
Michelle Obama
1964
lawyer and former First Lady of the United States (2009-2017)
Harrison Ford
1942
American actor (born 1942)
Bobby Fischer
1943–2008
American chess player (1943–2008)
James Watson
1928–2025
American molecular biologist, geneticist, zoologist and Nobel Laureate (1928–2025)
Anastacia
1968
American singer
Gillian Anderson
1968
American actress (born 1968)
Landmarks & Historic Sites
Attractions and heritage-registered places located in Chicago, IL.
Willis Tower
skyscraper in Chicago, Illinois
Art Institute of Chicago
art museum and school in Chicago, United States
Wrigley Field
baseball stadium in Chicago, Illinois, USA; home venue of the Chicago Cubs
Field Museum of Natural History
natural history museum in Chicago, Illinois, United States
Kenneth C. Griffin Museum of Science and Industry
museum in Chicago, Illinois, United States
City data from Wikidata (Q1297), available under CC0. Photos from Wikimedia Commons under their respective licenses. See our methodology for details.
Traveler Guide to Chicago, IL
Chicago is the home of the blues and the truth of jazz, the heart of comedy and the idea of the skyscraper. Here, the age of railroads found its center, and airplanes followed suit. "Stormy, Husky, Brawling / City of Big Shoulders," Chicago is a Heartland boomtown, its ethos defined by urban planner Daniel Burnham's immortal vision: "Make no little plans; they have no magic to stir men's blood." It is one of the world's great cities and the third largest city in the United States, behind only New York City and Los Angeles. As the hub of the Midwest, Chicago is easy to find — its picturesque skyline calls across the waters of Lake Michigan, a first impression that soon reveals world-class museums of art and science, miles of sandy beaches, huge parks and public art, and perhaps the finest downtown collection of modern architecture in the world.
Chicago tourist information. Chicago was known as a fine place to find a wild onion if you were a member of the Potawatomi tribe, who lived in this area of Illinois before European settlers arrived. It was mostly swamps, prairie and mud long past the original settlement by Jean Baptiste Point du Sable in 1779, the establishment of Fort Dearborn in 1803 and incorporation as a town in 1833. It could be argued that nature never intended for there to be a city here; brutal winters aside, it took civil engineering projects of unprecedented scale to establish working sewers, reverse the flow of the river to keep it out of the city's drinking supply, and stop buildings from sinking back into the swamps — and that was just the first three decades. Chicago became a waypoint between the Great Lakes and the Wild West, where boats came to drop off settlers, and load crops and other goods from the Great Plains and the Rocky Mountains. By 1871, the reckless growth of the city was a sight to behold, full of noise, Gothic lunacy, and bustling commerce. But on October 8, the Great Chicago Fire quickly spread through the city, killing 300 and destroying the oldest part of the city. A journalist blamed it on Mrs. O'Leary and her cow, but years later admitted that he invented the story. The stone Water Tower in the Near North is the most famous surviving structure. But the city seized this destruction as an opportunity to rebuild bigger than before, giving canvas for several architects and urban planners who would go on to become legends of modern architecture.
Along the Magnificent Mile — one day and night in Chicago, with skyscrapers, shopping, food, parks, and amazing views of the city from high and low. Loop Art Tour — a 2- to 4-hour walking tour of downtown Chicago's magnificent collection of modern sculptures. Chicago's set of museums and cultural institutions are among the best in the world. Three of them are within a short walk of each other in the Near South, on what is known as the Museum Campus, in a beautiful spot along the lake: the Adler Planetarium, with all sorts of cool hands-on space exhibits and astronomy shows; the Field Museum of Natural History, which features SUE, the most complete Tyrannosaurus rex skeleton ever found, and a plethora of Egyptian treasures; and the Shedd Aquarium, with dolphins, whales, sharks, and the best collection of marine life east of California. A short distance away, in Hyde Park, is the most fun of them all, the Museum of Science and Industry — or, as generations of Chicago-area grammar school students know it, the best field trip ever. Also in Hyde Park is the University of Chicago, whose Oriental Institute is one of the world's foremost authorities on Ancient Near East archaeology, and operates a free museum displaying its archaeological findings. The Museum of Science and Industry has a transportation exhibit and a weather exhibit. Visitors can even control a tornado with the joystick controller desk.
Chicago is not known as a beach destination, but Lake Michigan is the largest freshwater lake that is entirely within the United States, and Chicagoans flock to its sandy shores. Anyone can show up and swim — there are no admission fees, miles of beaches are within walking distance of the Red Line, and almost none of the lakefront is spoiled by "private" beaches. Despite the latitude, the water is quite warm in the summer and early fall (check with the NWS for temperatures). The Chicago shore has been called the second cleanest urban waterfront in the world, although bacteria levels in the water do force occasional — but rare — beach closures (which are clearly posted at the beach, and online. Lifeguards will be posted (usually in a rowboat) if the beach is officially open. Oak Street Beach and North Avenue Beach (in the Near North and Lincoln Park) are the fashionable places to sun-tan and be seen, but Rogers Park has mile after mile of less pretentious sand and surf. Hyde Park's Promontory Point is beautiful, and offers skyline views from its submerged beach by the rocks. Swimming there is against city rules, but it appears this is not enforced. Hollywood Beach in Edgewater is the main gay beach. Navy Pier was built in 1914 and served as a naval base during both world wars. It is now Illinois' number one most visited tourist attraction (ahead of some boring exurban megamalls). The pier has carnival rides, including the popular Ferris wheel, as well as theater, restaurants, arcades, bars, shops, and most importantly great views back towards the city.
Chicago is one of the great restaurant towns in America. If you're looking for a specific kind of cuisine, check out the neighborhoods. Greektown, the Devon Ave Desi corridor, Chinatown, and Chatham's soul food and barbecue are just the tip of the iceberg. Other areas are more eclectic: Lincoln Square and Albany Park have unrivaled Middle Eastern, German, and Korean food, while Uptown offers nearly the whole Southeast Asian continent with Ghanaian, Nigerian, contemporary American, stylish Japanese, and down-home Swedish a few blocks away. Despite the relatively small size of the Jamaican community, they have also left an indelible mark on the local culinary scene, with numerous Jerk restaurants scattered throughout the city. If you're interested in celebrity chefs and unique creations, Lincoln Park and Wicker Park have plenty of award-winners. River North has several good upscale restaurants, but don't waste your time on tourist traps or national chain restaurants. In fact, you should never submit to standing in line — there are always equally good restaurants nearby. No matter what you enjoy, you'll have a chance to eat well in Chicago, and you won't need to spend a lot of money doing it — unless you want to, of course. But while Chicago has a world class fine dining scene, it is the low-end where it truly distinguishes itself. No other city on earth takes fast food so seriously; for those who don't concern themselves with calorie counting, Chicago is cheap, greasy heaven.
Chicago is a drinking town, and you can find bars and pubs in every part of the city. It is believed that Chicago has the second highest number of bars per capita in the U.S. (after San Francisco). Unlike many other big cities where the hottest clubs are sought after, Chicago locals much prefer the dive bars and many don't seem to particularly like staying in one place. Most areas that thrive on the bar culture do so for the variety, and bar hopping is the norm. Grab a drink or two, then try the place next door. It is all about variety. Be prepared to be asked for identification to verify your age, even at neighborhood dive bars. Smoking is banned in Chicago bars (and restaurants). The best places to drink for drinking's sake are Wicker Park and neighboring Logan Square and Bucktown, which have a world-class stock of quality dive bars and local craft breweries. North Center and Roscoe Village are also a great (and underrated) destination for the art of the beer garden. Beware the bars in Lakeview near Wrigley Field, though, which are packed on weekends, and jam-packed all day whenever the Cubs are playing. Just to the south, Lincoln Park has bars and beer gardens to indulge those who miss college, and some trendy clubs for the neighborhood's notorious high-spending Trixies. Ill-informed tourists converge upon the nightclubs of State and Division Streets. The city's best DJs spin elsewhere, the best drinks are served elsewhere, and the cheapest beers are served elsewhere; the hottest of-the-moment clubs and in-the-know celebrities are usually elsewhere, too.
Chicago hosts many major conventions each year and has plenty of places to stay. The majority are either at O'Hare Airport or downtown in the Loop and the Near North (near the Magnificent Mile). If you want to explore the city, aim for downtown — a hotel near O'Hare is good for visiting one thing and one thing only, and that's O'Hare (although the CTA Blue Line is walking distance from most of them, so access to the city is easy, aside from 30 minutes). However, if you have a specific interest in mind, there are hotels throughout the city, and getting away from downtown will give you more of a sense of other neighborhoods. You'll appreciate that if you're in town for more than a couple of days. Make sure that where you're staying is within your comfort level before committing to stay there, though. More far flung transient hotels will be suitable for those seeking to relive Jack Kerouac's seedy adventures around the country, but may alarm and disgust the average traveler. Budget-priced places are usually pretty far from the Loop, so when you're booking, remember that Chicago is vast. Travelers on a budget should consider accommodations away from the city center which can be easily reached via any of the several CTA train lines. There is a hostel in the Loop with another hostel by Wrigley Field, a hostel in Greektown within walking distance to Union Station and two others near the universities in Lincoln Park and Rogers Park, all of which are interesting neighborhoods in their own right, and close to the L for access to the rest of the city.
Chicago (CHI IATA for all airports) is served by two major airports: O'Hare International Airport and Midway International Airport. There are plenty of taxis both to and from the city center, but they are quite expensive, especially during rush hours. Expect upwards of $40 for O'Hare and $30 for Midway. CTA trains provide direct service to both larger airports for $2.50 from anywhere in the city — faster than a taxi during rush hour and a lot less expensive. (Train rides originating at O'Hare are $5.) Many large hotels offer complimentary shuttle vans to one or both airports, or can arrange one for a charge ($15–25) with advance notice. O'Hare International Airport (ORD IATA) is 17 miles (27 km) northwest of downtown and serves many international and domestic carriers. United Airlines has its main hub here and is the airport's main airline; American Airlines is second at O'Hare. Most connecting flights for smaller cities in the Midwest run through O'Hare. It's one of the biggest airports in the world, and it has always been notorious for delays and cancellations. It is too far northwest for most travelers who get stuck overnight to head into the city, but there are plenty of hotels in the O'Hare area. See the O'Hare article for listings. The CTA Blue Line runs between the Loop and O'Hare at least every 15 minutes, 24 hours a day and 7 days a week. A trip on the Blue Line from O'Hare to the Loop takes around an hour. The O'Hare station is the end of the line and is essentially in the basement of O'Hare airport.
Navigating Chicago is easy. Block numbers are consistent across the whole city. Standard blocks, of 100 addresses each, are roughly 1/8th of a mile (200 meters) long. (Hence, a mile is equivalent to a street number difference of 800.) Each street is assigned a number based on its distance from the zero point of the address system, the intersection of State Street and Madison Street. A street with a W (west) or E (east) number runs east-west, while a street with a N (north) or S (south) number runs north-south. A street's number is usually written on street signs at intersections, below the street name. Major thoroughfares are at each mile (multiples of 800) and secondary arteries at the half-mile marks. Thus, Western Ave at 2400 W (3 miles west of State Street) is a north-south major thoroughfare, while Montrose Ave at 4400 N is an east-west secondary artery. In general, "avenues" run north-south and "streets" run east-west, but there are numerous exceptions. (e.g., 48th Street may then be followed by 48th Place). In conversation, however, Chicagoans rarely distinguish between streets, avenues, boulevards, etc. Several streets follow diagonal or meandering paths through the city such as Clark St, Lincoln Ave, Broadway, Milwaukee Ave, Ogden Ave, Archer Ave, Vincennes Ave, and South Chicago Ave. The best way to see Chicago is by public transit. It is efficient in terms of price, travel time, and safety. The Regional Transportation Authority (RTA) oversees the various public transit agencies in the Chicagoland area.
As in almost the entire United States, dial 911 to get emergency help. Dial 311 for all non-emergency situations in Chicago. Despite a big decline in the crime rate from the 1970s and 1980s, Chicago is still a big city with big city problems. There are run-down areas within a few blocks of some well-traveled places such as near the United Center and Rate Field. The majority of the city's violent crimes occur within a relatively small number of deeply impoverished neighborhoods well off the beaten path in the South and West Sides, but given the chance nature of crime, you should exercise the usual precautions wherever you go. Even in a neighborhood with a bad reputation, though, you might still have a perfectly good time, as long as it falls within your comfort level. Take caution in the Loop at night; after working hours, the Loop gets quiet and dark in a hurry west of State Street, but you'll be fine near hotels and close to Michigan Avenue and the lake. When disembarking a crowded CTA train, especially in the downtown-area subways, be wary of purse snatchers. Homelessness is a problem in the city and seeing people ask for help is common downtown. They are very unlikely to pose any kind of problem, though. Most are either holding up a sign asking for some type of assistance while others will actively solicit you for spare change. If you ignore them, they will ignore you. Some do sell a local newspaper called Streetwise to make a living. These people should be wearing a badge of some kind to indicate they sell the newspaper and they keep all the profits they make.
Travel tips adapted from Chicago on Wikivoyage, licensed CC BY-SA 4.0. Content summarized; visit the source for the full article. See our methodology for how we use it.
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