Chicago Holidays

Chicago is the American city that does it all with a grin: cloud-scraping architecture, world-beating pizza and blues bars that go till late. And because it sits on a freshwater sea, your city break comes with actual beaches.

Highlights of your Holidays to Chicago

• That skyline - Home of the skyscraper and still showing off: ride to the Willis Tower Skydeck, walk the Riverwalk, or see it all from an architecture river cruise, the city's best 90 minutes

• Deep dish and beyond - The famous pizza is a knife-and-fork event, but Chicago's food scene runs from Italian beef sandwiches to some of America's most exciting restaurants

• Music in its bones - The home of house music and electric blues does live gigs every night of the week, from century-old jazz rooms to summer's giant Lollapalooza festival

• Lake Michigan beaches - 26 miles of free lakefront with proper sandy beaches minutes from downtown, a city break that packs a swim

• World-class museums - The Art Institute, the Field Museum's T. rex and the Shedd Aquarium cluster around downtown, rainy days sorted

• Big-league sport - Baseball at century-old Wrigley Field is the classic summer afternoon, and this town takes its teams personally

Good to Know

• ☀️ Weather - A city of proper seasons: summers in the high 20s°C made for the lakefront, crisp golden autumns, snowy sparkling winters and a fresh, flowery spring

• 💰 Money - A sit-down meal runs £15-£20 / €17-€23, a beer is £5-£6 / €6-€7, and a deep dish pizza feeds two for around £20 / €23 (arrive hungry, it's a commitment)

• 🌊 Fun Fact - In 1900 Chicago's engineers reversed the entire flow of the Chicago River, and every St Patrick's Day the city dyes it bright green anyway, just to show who's boss

Chicago is perfect for you if...

• You want New York energy with Midwest manners, shorter queues and friendlier bills

• Your ideal night out involves a blues bar, a comedy club and a rooftop with a skyline, though maybe not in that order

• You take pizza seriously enough to have opinions about deep dish versus thin crust

• You want a big American city break that sneaks in a beach afternoon

• You plan holidays around food and would happily queue for a sandwich with a cult following

🏨 Hotels

From grand old institutions opposite Millennium Park to sleek towers over the Magnificent Mile, Chicago's hotels are an attraction in their own right. See all hotels in Chicago or browse our top picks below...

👨‍👩‍👧‍👦 What are the best family hotels in Chicago?

• Best Western River North Hotel is the family sweet deal: an indoor heated pool for the post-museum wind-down and a River North spot that keeps deep dish and the L close.

• Hilton Garden Inn Chicago Downtown Riverwalk sits steps from the Riverwalk with Maggie Daley Park's climbing walls and mini golf nearby, the easiest yes in the family vote.

• Eurostars Magnificent Mile keeps the crew near the big shops, the beaches and Navy Pier's Ferris wheel, with well-reviewed rooms that swallow a family's luggage.

💑 What are the best hotels in Chicago for couples?

• Chicago Athletic Association is a date night disguised as a hotel: a gorgeous 1890s athletic club opposite Millennium Park, all dark wood, games rooms and a rooftop looking over the Bean.

• Kimpton Gray Hotel does sleek marble style in the Loop with a buzzy rooftop bar, close enough to the Riverwalk for a hand-in-hand wander.

• Sofitel Chicago Magnificent Mile brings French polish to the Gold Coast, a striking glass prism with a spa and a very good bar for a pre-dinner cocktail.

✨ What are the best luxury hotels in Chicago?

• The Peninsula Chicago is the city's five-star benchmark: an indoor pool with skyline views, a serious spa and service that remembers your name, right on the Magnificent Mile.

• Waldorf Astoria Chicago hides Parisian-style courtyard glamour in the Gold Coast, with an award-winning spa and an indoor lap pool for the morning after.

• Sofitel Chicago Magnificent Mile earns its luxury slot on architecture alone, a wedge of glass that's one of the city's most admired modern buildings, with the rooms to match.

👉 All hotels in Chicago

What are the best beaches in Chicago?

Here's Chicago's best-kept secret from first-time visitors: it's a beach city. Lake Michigan is a freshwater sea with a horizon, and 26 miles of free public lakefront run right along the skyline.

• North Avenue Beach is the headliner, wide sand, volleyball courts and a beach house shaped like an ocean liner, with the skyline photobombing every picture

• Oak Street Beach brings towel-to-towel summer glamour at the foot of the Gold Coast, the closest thing the Midwest has to a Riviera

• Ohio Street Beach is the calm, family-friendly cove near Navy Pier, handy for a quick paddle between sights

The water's freshest early summer and properly warm by August, and the lakefront trail beside the sand does sunrise runs and sunset strolls all year.

Cheap holidays to Chicago

Chicago might be the best-value big city break in America, because so much of the good stuff is free: the lakefront and every one of its beaches, Millennium Park and the Bean, the Riverwalk, Lincoln Park Zoo (genuinely free, genuinely great) and the summer calendar of free festivals and outdoor gigs. Add the Blue Line train running straight from O'Hare to downtown for a few dollars and you've skipped the airport-taxi tax before the holiday's even started.

Eating well cheaply is a local art form. Deep dish feeds a table for the price of one fancy main, Italian beef sandwiches and classic hot dog stands do lunch for pocket money, and happy hours run generous in River North. If you're stacking up the big paid attractions (Skydeck, the museums, the aquarium), the multi-attraction passes cut the total substantially, so tally your hit list before buying tickets one by one.

Book early for summer festival weekends and school holidays, when the lakefront season fills the city, and keep an eye on low-deposit deals so the upfront cost stays tiny while your budget goes on pizza and blues bars.

Chicago Holidays 2026/2027 - Travel Guide

👨‍👩‍👧‍👦 What are the best things to do on a Chicago family holiday?

• Navy Pier - Ferris wheel, boat rides, fireworks in summer and a children's museum, the all-day family default

• The Field Museum - Home of Sue, the most complete T. rex ever found, and a dinosaur hall that turns kids into palaeontologists

• Shedd Aquarium - Belugas, otters and a shark tunnel on the lakefront museum campus, pair it with the neighbouring museums for a full day

• Maggie Daley Park - Free climbing walls, rope bridges and a skating ribbon in winter, the city's best playground with a skyline backdrop

• North Avenue Beach afternoon - Buckets, spades and volleyball with skyscrapers watching, the holiday photo nobody expects from Chicago

💑 What are the best things to do for couples on a Chicago holiday?

• Architecture river cruise - Ninety minutes of gliding past the world's most famous skyline while a guide tells you what you're looking at, the city's essential date

• The Art Institute - One of the world's great galleries, from Monet to American Gothic, with leafy Millennium Park on its doorstep

• Green Mill jazz - A century-old jazz room with a speakeasy past, dimly lit and utterly transporting

• Sunset from a rooftop bar - The skyline does its best work at golden hour, and downtown's rooftops queue up to serve it with a cocktail

• The Riverwalk - Wine bars, gelato and boat-watching along the water, made for a slow evening wander

🎉 What are the top things to do for groups on a Chicago holiday?

• Wrigley Field - An afternoon of baseball, beers and singalongs at one of America's oldest ballparks, no rules knowledge required

• Lollapalooza - The giant four-day festival takes over Grant Park each summer (July 30 to August 2 in 2026), book the whole trip around it

• Second City comedy - The legendary improv theatre that launched half of American comedy, a guaranteed great group night

• Blues bar crawl - Electric blues was practically invented here and the clubs still go late, follow the guitars

• Beach volleyball at North Avenue - Summer courts, big crowds and a post-game beach bar, the group afternoon that organises itself

What should foodies eat on a Chicago holiday?

• Deep dish pizza - The famous knife-and-fork pie, thick, cheesy and gloriously excessive, split one between two and cancel dinner plans

• Italian beef sandwich - Thin-sliced beef dunked in gravy on a soft roll, order it "dipped" and lean forward when you bite

• A proper Chicago dog - All-beef frankfurter dragged through the garden (mustard, relish, onions, tomato, pickle, peppers), and absolutely no ketchup

• Garrett popcorn - The cheese-and-caramel "Garrett Mix" is the city's sweet-salty obsession, the queue moves fast

• West Loop restaurant row - The city's buzziest dining strip, where the hard part is picking just one reservation

More Destinations

• America - The parent page for the whole US adventure: city breaks, beach weeks, national parks and road-trip legends coast to coast

• New York - The city that never sleeps: Broadway lights, Central Park mornings and skyline views that need no introduction

• Las Vegas - Neon, mega-resorts, world-famous shows and the Grand Canyon within day-trip distance

• Orlando - The theme park capital of the world: Walt Disney World, Universal and more waterslides than any sensible city needs

• Miami - Art deco glamour, Cuban coffee, golden sand and a nightlife scene that never got the memo about bedtime