Chicago
Chicago is the city that invented the skyscraper, on an inland sea that behaves like one, with an elevated railway that is a sight in itself and a lakefront path eighteen miles long. Two or three nights, the river cruise first, and no ketchup on the hot dog.
Chicago in a nutshell
Chicago: what to expect
Before writing this we counted 450,000+ planned stops across the United States on Stippl.
Chicago is an architecture city before it is anything else, and two or three nights sees it from the river, the ground and the air. The boat cruise along the three branches of the river is the standard way to see the buildings, Millennium Park and Cloud Gate sit free in the middle of the Loop, the Art Institute holds one of the great collections, the lakefront path runs eighteen car-free miles, and the blues rooms play seven nights a week. Most travellers give Chicago 2 nights on Stippl.
Chicago is planned as a start more than an end, and it has the widest tail of any American city. The city opens 44.5% of the trips it appears on, of everyone who plans it on Stippl, and 21.4% of Chicago stops run to four nights or more, alongside 27.5% that are a single night, which is a city that rewards whoever gives it the time.
Sleep in the Loop or River North, take the Blue Line in from O'Hare, and do the river cruise first. The L reaches everything an itinerary needs and parking downtown is expensive. Skip Chicago between November and March unless the museums are the point, because the winter here is not a mood but a fact, and skip the idea that the city is dangerous where visitors go, since the crime is concentrated in neighbourhoods no itinerary passes through.
Plan Chicago in Stippl
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Download the appWho Chicago is for
First-timers
One legible grid, one elevated railway and the country's best free park at the centre of it, with the river cruise as the orientation.
History buffs
The fire, the fair, the stockyards, the Great Migration and the birth of the skyscraper, all still visible on the street and in the museums.
Foodies
A deep restaurant city that is not priced like a coastal one, from Italian beef on a roll to the tasting menus of the West Loop.
Art lovers
The Art Institute is a top-five collection anywhere, and the murals in Pilsen cost nothing.
Trip starters
Chicago opens 44.5% of the trips it appears on, of everyone who plans it on Stippl, as the midwestern door before the road west.
Long-stayers
21.4% of Chicago stops on Stippl run to four nights or more, the widest tail of any American city we measure.
Maybe not for you: anyone travelling between November and March who does not want to be cold, since the winter here is a fact rather than a mood; and anyone who wants the lakefront and the patios in the months they are shut.
The best time to visit Chicago
The warm half
May to October
Every festival, both beaches and all the patios, the lakefront path in use and the river cruises running: the city the pictures show.
High summer
July and August
The hottest, busiest and most humid months, with Lollapalooza in Grant Park and the Air and Water Show, and the two months most people actually pick.
The shoulder that wins
September and October
Warm days, cold nights, no queues and the clearest skies of the year, with the trees on the lakefront turning by mid-October.
Winter
November to March
Genuinely cold, genuinely snowy and genuinely cheap, with the museums as the reason to come and the river dyed green for St Patrick's Day at the end of it.
- Most travellers give Chicago 2 nights on Stippl, and 21.4% of stops run to four or more. Two covers the river, the park and a museum; the fourth night is the neighbourhoods and a ballgame.
- Most travellers plan Chicago about 102 days days ahead on Stippl, and 17.1% inside a fortnight. Nothing in the city sells out months ahead except the summer festival weekends and a Cubs game at Wrigley.
- The Chicago River is dyed green on the Saturday nearest 17 March. The city's single most photographed morning, with the riverwalk full by nine and the bars full by ten.
- Lollapalooza takes four days in Grant Park in late July or early August. Hotel prices across the Loop move for it, and the park is fenced for the week either side.
- The Air and Water Show in August is free and draws around a million people. A weekend over North Avenue Beach, with the lakefront path impassable and the jets rehearsing over the Loop on the Friday.
- June to September takes 51.3% of Chicago plans on Stippl. The people who come in September and October get the same city with the queues gone and the skies at their clearest.
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Things to do in Chicago
Photo by Hank Nielsen via Pexels
Photo by Patricia Jekki via Unsplash
Photo by Ela108 Garwacka-Goralik via UnsplashThe architecture river cruise
Ninety minutes along the three branches of the Chicago River with a trained docent naming the buildings, from the Wrigley Building to the corncobs of Marina City; the thing to do first.
Millennium Park and Cloud Gate
The mirrored sculpture everyone calls the Bean, in a free park in the middle of the Loop, with the Crown Fountain and the Pritzker Pavilion concerts on summer evenings.
The Art Institute of Chicago
One of the great collections, and the Impressionist rooms with the Seurat and the Hopper are the reason people stay a second day.
A view from above
The Skydeck's glass ledge at Willis Tower or 360 Chicago's tilting window at the old Hancock; one of the two, not both, and the Hancock has the lake.
The lakefront path
Eighteen miles of car-free waterfront, best on a rented bike, from the beaches of the north side to the museum campus and the planetarium's skyline view.
A blues or jazz night
The city's electric blues tradition still has rooms playing it seven nights a week, in Lincoln Park and on the south side, for the price of a drink.
The neighbourhoods of Chicago
The Loop
The downtown core
Inside the elevated tracks, with Millennium Park, the Art Institute, the river and every train line, and the business district that empties at night. For first visits.
Every sight and every line on foot, and quiet, corporate streets after dark.
River North
Restaurants, galleries, hotels
The densest concentration of good eating within walking distance of the Loop, with the galleries, the steakhouses and most of the city's hotel rooms. For food and convenience.
Dinner within walking distance and the hotel volume, at the highest room rates in the city.
Wicker Park
Independent, scruffy, musical
Record shops, coffee, vintage and the venues that made the city's guitar scene, on the Blue Line between O'Hare and the Loop. For nightlife and remote workers.
The best independent scene and a direct line to the airport, and a ride to the lake.
Lincoln Park
Leafy, residential, free at the zoo
The zoo and the conservatory cost nothing, the beach is at the end of the street, and the blues clubs are on the avenue. For families and the lakefront.
The park, the zoo and the beach for nothing, and a train or a long walk to the Loop.
Pilsen
Mexican Chicago, and the murals
Taquerías, the National Museum of Mexican Art and the best street art in the city, south-west of the Loop on the Pink Line. For food and murals.
The best cheap food and the murals, with few hotels and a train to everything else.
Hyde Park
University, museums, lakefront
The Museum of Science and Industry, the Robie House and the university's Gothic quads on the south side, with Obama's old street. For history and a quiet base.
The museums and the campus, and a longer ride to the Loop than the map suggests.
See every Chicago neighbourhood on one map
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Where to stay in Chicago
Sleep in the Loop or River North, the two default choices, and River North buys you dinner within walking distance where the Loop buys the trains; Wicker Park puts you on the Blue Line straight from O'Hare. Most travellers give Chicago 2 nights on Stippl, the Loop empties after the offices close, and the summer festival weekends move the room rates across downtown.
The Loop
€150–260
Business hotels that drop their rates at the weekend, €150 to €320 a double.
River North
€160–280
The city's hotel volume from boutique to chain, €170 to €380 a double.
Wicker Park
€110–190
Small hotels and apartments on the Blue Line, €110 to €220 a double.
Lincoln Park
€130–220
Guesthouses and mid-range hotels near the park, €130 to €260 a double.
Pilsen
€100–170
Apartments and a hostel or two among the murals, €80 to €160 a double.
Hyde Park
€120–200
A few hotels by the university and the museum campus, €120 to €240 a double.
What to eat in Chicago
A pie baked in a pan with the sauce on top, eaten with a knife
Thin roast beef on a roll, dipped in its own gravy
Poppy seed bun, seven toppings, and never ketchup
Mexican Chicago, and the city's deepest food tradition
An old stockyard city that still does the classic version
A bitter wormwood liqueur locals dare visitors to drink
Discover food spots in Stippl
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Chicago customs and what not to do
No ketchup on hot dogs
It is a real local rule and it is enforced by refusal at some stands; mustard, relish, onion, tomato, pickle, peppers and celery salt are the seven.
Tip 18 to 20 percent
In sit-down places and at the bar a dollar or two a drink, the same as the rest of the country, and the tax is added at the till.
Stand right on escalators
The Loop moves at commuter pace on weekday mornings, and the L platforms are where the pace shows.
North versus South is baseball
Cubs and White Sox, and it is the first thing a local will ask; Wrigley on the north side is the ballpark visitors go to.
Deep dish once
It is the experience, not the city's daily pizza; tavern-style thin crust cut in squares is what Chicago actually eats.
The lake sets the weather
Weather arrives off Lake Michigan without warning, and a layer goes in the bag even in July.
Do
- Take the Blue Line in from O'Hare; it runs all night
- Do the river cruise first, as the orientation for everything else
- Rent a bike for the lakefront path
- Pick one tower, not both
- Eat one meal in Pilsen
Don't
- Put ketchup on a hot dog
- Drive downtown; the L reaches everything and parking is expensive
- Book November to March expecting the lakefront and the patios
- Pay for both observation decks
- Leave the layer at the hotel; the lake changes the weather in an hour
What a Chicago trip costs
Budget
€70–110
A hostel bed, the L on a Ventra card, hot dogs and tacos, the free park, the zoo and the lakefront.
Mid-range
€129–189
A mid-range hotel in the Loop, the river cruise, the Art Institute, one tower, a blues night.
High-end
€250+
A River North hotel, a West Loop tasting menu, Cubs tickets and a boat of your own on the river.
Track what you actually spend
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Fun facts about Chicago
The Chicago River was made to flow backwards in 1900. Engineers reversed it away from Lake Michigan to stop the city's sewage reaching its own drinking water, and it still runs that way.
The first steel-frame skyscraper went up in Chicago in 1885. Which is why the architecture cruise is the city's signature rather than a sideline.
Eighteen miles of Chicago's lakefront are public, end to end. Almost none of it is private, by a rule the city's planners wrote into the lakefront a century ago.
The Red and Blue Line trains in Chicago run 24 hours a day. Almost no other American metro does, which is why a late flight into O'Hare still gets you downtown.
Cloud Gate is 110 tonnes of stainless steel with no visible seams. Anish Kapoor's sculpture in Millennium Park was polished for two years after it was welded, and everyone still calls it the Bean.
The Chicago hot dog carries seven toppings and never ketchup. Mustard, relish, onion, tomato, a pickle spear, sport peppers and celery salt, on a poppy-seed bun.
Local tips for Chicago
One fare, one exception
The L and the bus cost about two euros on a Ventra card or a contactless bank card, transfers are free for two hours, and only the Blue Line from O'Hare costs more.
Two L lines run all night
Red and Blue are 24 hours, which is unusual in America and worth knowing before booking a late flight.
Tap a bank card
A contactless card skips the Ventra card entirely, and the Ventra card refunds its own cost if registered within ninety days.
The danger is not where you go
Chicago's violent crime is concentrated in specific south and west side neighbourhoods; the Loop, River North, Lincoln Park, Wicker Park and the lakefront are ordinary American city centre.
Ordinary big-city rules
Phone away on the L late at night, bags watched in crowded stations, and nothing more than that.
Two nights, or four
Most travellers give Chicago 2 nights on Stippl and 21.4% of stops run to four or more, the widest tail of any American city, so the third day is Pilsen or Hyde Park.
Chicago questions, answered
Two or three, with a long tail: most travellers give Chicago 2 nights on Stippl, and 21.4% of stops run to four or more, the widest tail of any American city we measure. Two covers the river, the park and a museum; the extra days are Pilsen, Hyde Park, a ballgame and the lakefront by bike.
For the areas visitors use, yes. The city's violent crime is concentrated in neighbourhoods no itinerary passes through, and the Loop, River North, Lincoln Park, Wicker Park and the lakefront are ordinary American city centre, with the ordinary rules about phones and bags on the L late at night.
As the midwestern door: Chicago opens 44.5% of the trips it appears on, of everyone who plans it on Stippl, with Route 66 west and the train to New York east. Put it into Stippl with three nights, then ask people who have done the Midwest, in subreddits like r/chicago, what to add.
September, then May and October: warm days, cold nights, no queues and the clearest skies of the year. July and August are the busiest and most humid, and the two months most people actually pick, with Lollapalooza and the Air and Water Show inside them.
Deep dish once, for the experience, with a knife and a long wait. Tavern-style thin crust cut in squares is what the city eats on a weeknight, and the Italian beef and the seven-topping hot dog are the other two local plates worth the detour.
No. The L reaches everything an itinerary needs, two lines run all night, the Blue Line comes in from O'Hare, and parking downtown is expensive. 9.6% of Chicago stops planned on Stippl are same-day, and even those work on the train.
Every guide is written by the Stippl editors and checked against the trips our travellers actually plan. Spotted something out of date? Let us know.
Plan Chicago in Stippl
Day-by-day planning, stays and budget in one app, with every place from this guide already on the map.
Download the app