Chicago travel guide
Where to stay, the best time to visit, what a day costs, and the traps to skip.
Things to do in Chicago, planned over three days
Best time to visit Chicago
• a note or something on ✦ an occasion worth the trip
Winter turns inward. Cruises stop, beaches are icy, but museums are quietest and conservatories, clubs and Second City work. Mid January to late February is worst.
Volatile, improving spring. March has the St. Patrick's river dyeing, April is mud season, and by May patios and the lakefront reopen before peak prices.
Peak Chicago. Beaches open Memorial Day to Labor Day, festivals are relentless, boats and rooftops at their best, and it is the most crowded and expensive.
Locals' favourite. September is warm, dry and still lakefront, with festival crowds gone. October brings fall colour, the Marathon and a real chill late.
The shoulder to skip. Cold and grey, not yet festive until Christkindlmarket opens late in the month.
Best months overall are September to early October, then late May to June.
What's on
- Christkindlmarket late November to December
German style Christmas market at Daley Plaza with mulled wine in a collectible boot mug.
- ZooLights late November to December
Festive lights season at Lincoln Park Zoo alongside Christkindlmarket and Millennium Park skating.
- Chicago Restaurant Week January to February
A locals' reason to leave the house in the coldest weeks.
- Chicago Theatre Week January to February
Discounted theatre across the city in the deep winter weeks.
- St. Patrick's Day river dyeing mid-March
The river dyed green with huge crowds. Book early.
- Chicago Blues Festival June
Free blues across several stages in Millennium Park, the biggest free blues festival in the world.
- Chicago Pride June
Pride Fest on Halsted and the parade through Lakeview on the last Sunday of June.
- Summerfest late June to early July
Billed as the world's largest music festival, in Milwaukee, worth timing the day trip around.
- Windy City Smokeout July
Country music and barbecue outside the United Center.
- Lollapalooza early August
Grant Park festival. Hotel prices spike citywide and the park closes to non ticket holders.
Worth the trip for
Best things to do in Chicago
Chicago Architecture Center River Cruise aboard First Lady
Ninety minutes on the river with a docent explaining the skyscrapers as you pass them at water level.
Art Institute of Chicago
One of the great art museums anywhere, from Impressionists to American Gothic and Nighthawks.
Millennium Park
Cloud Gate, Crown Fountain and Lurie Garden in the free downtown park everyone should walk once.
Chicago Riverwalk
A 1.25 mile riverfront walk of wine bars, kayak rentals and the best free people watching downtown.
Chicago Cultural Center
Free landmark with the world's largest Tiffany glass dome that most tourists walk straight past.
Wrigley Field
Ivy walled 1914 ballpark in a residential neighbourhood that turns into a street party on game days.
The Second City
The improv institution that launched half of modern American comedy, best at the Mainstage revue.
Garfield Park Conservatory
Huge free conservatory, warm all year, and the locals' top answer for a February day with visitors.
Where to stay in Chicago
River North
first trip, all-round base
Densest cluster of steakhouses, bars and late night options, walkable to the Riverwalk and downtown sights.
Gold Coast
couples, luxury and quiet
Tree lined old money streets just north of River North, a short walk to Oak Street Beach and the lake.
The Loop
theatre, architecture and value
Art Institute, Millennium Park and every CTA line, but many streets empty out at night once offices close.
West Loop / Fulton Market
foodies
Restaurant Row on Randolph and the city's buzziest tables, more local and less touristy than River North.
Lincoln Park
families and a calmer trip
Zoo, conservatory, lakefront and leafy streets 15 minutes north of downtown, thinner on hotels and late nights.
Wicker Park / Logan Square
local-feel, nightlife and cafes trip
Where younger Chicago eats, drinks and sees bands, on the Blue Line to O'Hare, with very few hotels.
Think twice about
- The O'Hare corridor / airport hotels
Isolated office park sprawl with no neighbourhood or restaurants on foot and a 45 minute train ride each way.
- South Chicago and Midway area motel strips
Vaguely marketed cheap bases far south or west with long, transit poor distances to everything.
- Englewood, Austin and North Lawndale
Persistently high rates of gun violence, almost no visitor infrastructure, and long distances from the sights.
- Indiana (Hammond/Gary) or far suburbs sold as Chicago
You will spend the trip commuting and pay for it in parking and time instead of seeing the city.
Best restaurants in Chicago
Smyth
Farm driven tasting menu from the Shields team, named one of North America's best.
Kasama
Filipino bakery cafe by day and a two star tasting menu by night, the first starred Filipino spot.
Bavette's Bar & Boeuf
Dim, jazzy French inflected steakhouse, the city's best steak and its hardest useful reservation.
Monteverde
Handmade pastas made in view of the dining room, the West Loop dinner locals recommend most.
Virtue
Refined Southern cooking in Hyde Park, with gulf shrimp and grits and legendary biscuits.
Au Cheval
The famous single cheeseburger that is really a double, in a dark diner glam room on Randolph.
Small Cheval
Counter service sibling in Bucktown serving the same Au Cheval burger with no long wait.
Pequod's Pizza
Pan pizza with a caramelised cheese crust edge, the pizza Chicagoans name when asked for their own pick.
Outdoor things to do in Chicago
Urban Kayaks
Paddle the canyon of towers yourself on a guided historic or sunset tour from the Riverwalk.
Kayak Chicago
Well regarded alternative for river paddles and beach launches at North Avenue and Montrose.
Tall Ship Windy
Sail a 148 foot schooner beyond the breakwater from Navy Pier and help raise the sails.
Come Sailing
Private sunset charter from Navy Pier marina, bring your own food and drink and sit on the bow.
Chicago SUP
Stand up paddleboarding on Lake Michigan with the skyline behind you, lessons and rentals included.
Bobby's Bike Hike
Relaxed guided rides along the lake and through Gold Coast and Lincoln Park, ideal on day one.
Harborside International Golf Center
Two links style 18s by Lake Calumet, the serious public round you can play without leaving Chicago.
Cog Hill Golf & Country Club
Dubsdread No. 4 in Lemont, a former PGA Tour stop and one of America's great public courses.
Best hotels in Chicago
The Peninsula Chicago
The splurge standard bearer on the Mag Mile, with huge rooms, attentive service and the Z Bar rooftop.
The Langham, Chicago
Luxury in the Mies IBM tower on the river, with the best river view rooms downtown and a top spa.
Virgin Hotels Chicago
Design forward mid price option near the Loop and River North edge, good value outside peak weekends.
Pendry Chicago
Luxury rooms in the gold-topped Art Deco Carbide and Carbon Building on Michigan Avenue, a block from Millennium Park.
Freehand Chicago
Hostel hotel hybrid in a 1927 River North building, the budget way into the best base area.
Waldorf Astoria Chicago
Quiet, Parisian feeling luxury with enormous rooms and fireplaces, away from Mag Mile crowds.
Viceroy Chicago
Younger, livelier Gold Coast hotel with a rooftop pool and bar that is a real summer asset.
The Hoxton, Chicago
The foodie base in Fulton Market, with Cabra rooftop and Restaurant Row outside the door.
Is Chicago expensive? What a day costs
| Budget | $170 a person |
|---|---|
| Classic | $320 a person |
| Splurge | $700 a person |
A day of food, drink, sights and getting around, before the room
What to book ahead
- Chicago Architecture Center River Cruise aboard First Lady: a few days ahead
- Art Institute of Chicago: a few days ahead
- Wrigley Field: a few days ahead
- The Second City: a few days ahead
- Kingston Mines: a few days ahead
- Heli Chicago: weeks ahead
- Urban Kayaks: a few days ahead
- Kayak Chicago: a few days ahead
- Bavette's releases 21 days out at 9am, Kasama dinner about 45 days out, and Smyth, Alinea and Oriole book weeks to months ahead.
- Book the CAC river cruise days ahead in summer, plus Second City weekends, sunset deck slots and Wrigley weekend games.
- Hotel prices spike for Lollapalooza in early August, the Chicago Marathon in October, big conventions and St. Patrick's Day weekend.
Is Chicago safe?
- Tourist Chicago is busy and walked by locals day and early night. The real risks are phone snatches, pickpocketing in crowds and car break-ins.
- Leave nothing visible in a car, ever, and use the official taxi line or rideshare pickup at O'Hare, not solicited rides inside.
- After midnight take rideshare door to door instead of waiting on empty platforms, and avoid deserted Loop side streets at 1am.
Chicago travel tips: tourist traps to skip
- Navy Pier, a long pier of chain food and souvenir markup. Go only for the wheel view or the summer fireworks from the lakefront.
- Giordano's or Uno as the pizza pilgrimage. Pequod's is the local pick and Lou Malnati's the classic deep dish alternative.
- Doing both observation decks, especially in rain or fog. Pick one deck on a clear day or spend the money on the river cruise.
- Magnificent Mile chain shopping at flagship prices, and eating deep dish more than once. Once, shared and sit down, is the experience.
Getting around Chicago: public transport and more
- Do not bring a car. Downtown hotel and garage parking runs roughly $40 to $75 a night and everything here is on the CTA.
- Tap any contactless card or phone on the CTA. The 3 day unlimited pass at about $15 pays for itself fast.
- From O'Hare take the Blue Line, 24 hours and about 45 minutes to the Loop. From Midway take the Orange Line, about 25 minutes.
- Use Divvy bikes for the Lakefront Trail and the 606, and the seasonal water taxi between the Loop, Museum Campus and Chinatown.
Who Chicago suits
| Solo travellers | Good |
|---|---|
| Groups of friends | Great |
| Couples | Great |
| Bachelor parties | Good |
| Families | Good |
| Bachelorette parties | Good |
Make Chicago your trip
Swearby drafts the days from places people swear by. Swap any stop, then invite the crew by text, even friends without the app. Vote on dates, track costs as you go, and everyone gets one number at the end.
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