Chicago

Chicago sits on the southwestern shore of Lake Michigan — incorporated as a city in 1837 on land the Potawatomi had ceded four years earlier — and grew because it happened to be the only reasonable point at which railroads from the East met the Great Lakes and the Mississippi River watershed. Everything ran through here: the grain, the cattle, the timber, the mail. If a river town could have been the center of the country’s economy, it would have been. Chicago was the compromise.

The downtown that stands today is built on top of two things: a raised grade and a fire. In the 1850s, engineers physically lifted downtown buildings about six feet out of the mud so proper sewers could go underneath. Twenty years later, in October 1871, the Great Chicago Fire burned a four-by-one-mile stretch of that same downtown, leaving 100,000 people homeless and clearing the field for what turned into the birthplace of the American skyscraper. By 1893 the city was hosting the World’s Columbian Exposition and drawing more than 27 million visitors. That is 22 years from ashes to world’s fair.

Modern Chicago is 77 official community areas across the North Side, the South Side and the West Side, connected by the L (the elevated rapid transit that gave the Loop its name) and the Chicago River, which the city famously reverses the flow of and dyes green every St. Patrick’s Day. It has six major professional teams whose home venue is inside city limits, more than 30 miles of continuous lakefront trail, and one of the great art museums in North America. It also has an ongoing pizza argument that will not be settled in your lifetime.

Millennium Park and the Art Institute are the anchor: the widest, easiest, most-photographed slice of downtown Chicago. Cloud Gate — the mirror-polished stainless-steel sculpture everyone calls the Bean — sits in the center of the plaza, with the Art Institute’s bronze lions guarding the doors half a block south. Behind them rises the Chicago skyline; below them opens the museum campus and the lakefront. From this one corner you can walk to more of the city’s must-sees than from any other.

*Fees subject to change, please check garfieldconservatory.org for updated information.

The Chicago food question isn’t deep dish or thin — it’s deep dish, tavern-style thin, or an Italian beef. Deep dish is baked in a cast-iron pan and filled with mozzarella, then covered with toppings and finished with a layer of tomato sauce, according to National Geographic. Lou Malnati’s says it has served deep dish since 1971, and Pequod’s describes a caramelized crust as its signature. Tavern thin — cracker-crust, cut into squares — is what actual Chicago families order on a weeknight; Vito & Nick’s on the south side is the classic order.

The Italian beef is the other Chicago sandwich argument: thin-sliced beef, gravy, giardiniera or sweet peppers, dipped or dry. Al’s Beef says its beef stand opened in 1938 in the Little Italy neighborhood and calls itself “the beefstand that launched the national sandwich of chicago.” The company lists its Taylor Street location at 1079 West Taylor Street, where it reopened in the early 1960s. For breakfast the answer is a Manny’s corned-beef sandwich or a Lou Mitchell’s omelette on West Jackson. Neither has changed much in seventy years.

41 breweries within 10 miles of Chicago, 16 of them brewpubs with a kitchen.

Brewpub locations from Open Brewery DB (MIT)

10 more Highway Heads places lie within about 180 miles of Chicago in a straight line — far enough that most are a night away rather than an afternoon.

• KenoshaWisconsinabout 50 mi
• South BendIndianaabout 75 mi
• MadisonWisconsinabout 120 mi
• Grand RapidsMichiganabout 130 mi
• Fort WayneIndianaabout 140 mi
• GalenaIllinoisabout 150 mi
• IndianapolisIndianaabout 160 mi
• Wisconsin DellsWisconsinabout 160 mi
• LansingMichiganabout 170 mi
• SpringfieldIllinoisabout 180 mi

• GIGANTARGiant statue / World's largestJolietabout 32 miles away

  Cost to see it

  Free

  When you can see it

  Any time — outdoors, visible from the road

  Nearest road

  Route 66

  24-foot guitar shaped like a Route 66 shield, lit at night.

  Read on the page we checked

• Gemini GiantGiant statue / World's largestWilmingtonabout 46 miles away

  Cost to see it

  Free

  When you can see it

  Any time — outdoors, visible from the road

  Nearest road

  Route 66 (IL-53)

  Space-helmeted Muffler Man holding a rocket, relocated to a park.

  Read on the page we checked

These are things you can go and look at, not a recommendation of any of them. Oddities move, get sold and quietly disappear more than anything else we list, so check anything you are driving a long way for. Some sit on private land and can only be seen from the road — please do not go onto anyone’s property. Every entry links the page we read it off.

Base downtown or in the Loop for a first visit. Everything scales out from there — Millennium Park, the Riverwalk, the Art Institute and the L are all inside a twenty-minute walk.

The L is the way to move. CTA says riders can tap a contactless bank card or a mobile device at the station gate, and cash can be used at a station vending machine to buy a fare card. Red Line and Blue Line train service operates 24 hours per day, every day, while most other train routes run from the early morning until the late evening. CTA lists these stops: Addison on the Red Line for Wrigley Field, the Roosevelt stops on the Red, Orange and Green Lines for Soldier Field, Illinois Medical District on the Blue Line for the United Center, and the Blue Line itself for O’Hare.

Game tickets. How quickly Cubs and White Sox games sell out could not be confirmed, so check each team’s ticket page before planning around a game. The Cubs say tickets are available exclusively as mobile tickets through the free MLB Ballpark app. CTA lists Wrigley Field as just a half block west of the Addison stop on the Red Line and the White Sox ballpark as just a block west of the Sox-35th stop on the same line.

Weather is honest. The wind off the lake is the point; from December to March, layer for it. Late April through October is the visitor-friendly window.

Millennium Park (Cloud Gate)

Address

201 E Randolph St, Chicago, IL 60602

Hours

Check the official site for current hours

Price

Free admission to the park

Link

chicago.gov/millennium_park

We checked fees, operating status, reservations and seasonal opening on 2026-10-15. These change without notice — confirm with chicago.gov, nationalmuseumofmexicanart.org, garfieldconservatory.org, navypier.org, soldierfield.com, transitchicago.com, mlb.com and griffinmsi.org the week you travel.

Straight-line distance from Chicago, not drive time.

• Chicago Midway International (MDW) — 7 miles
• Chicago O'Hare International (ORD) — 16 miles
• Gary/Chicago International (GYY) — 20 miles