Choose your preferred language. We speak English (US) and 42 other languages.
Chicago’s got the lot – Lollapalooza, Obama, Oprah and hot-dogs sans ketchup (a travesty? You be the judge!). This Midwestern monolith has a pumping arts scene, oodles of public space and 1001 reasons for a high-end spend. It's not that windy, but pack your woollies anyway.
32 ℉ 19 ℉
31 ℉ 19 ℉
45 ℉ 32 ℉
56 ℉ 42 ℉
69 ℉ 54 ℉
76 ℉ 62 ℉
80 ℉ 68 ℉
80 ℉ 67 ℉
75 ℉ 61 ℉
61 ℉ 49 ℉
48 ℉ 35 ℉
40 ℉ 30 ℉
Fly by the 9-5ers and straight to the Chicago Cultural Centre. Visceral, inspirational – look up at the triumphant Tiffany Dome – this building’s visitor centre is a plum resource for what’s hip and happening in the windy city. The Art Institute of Chicago’s elite collection is an essential stop, as is Magnificent Mile for shops-a-plenty.Accommodations in Downtown Chicago
Go loopdy-loop on ‘The Loop’ with bakers, bankers and holiday-makers. Downtown is a jostle-fest day in and day out because it’s home to the city’s top spots. Skip the skyscrapers, but see The Rookery’s ‘light court’ – architect Frank Lloyd Wright’s magnum opus. Dine with the ladies who lunch on Rush Street, or museum-hop ‘til the sun drops.Accommodations in Chicago Loop
The name says it all, darling. Bloomingdales, Saks Fifth, Neiman Marcus, Apple’s svelte flagship store and designer brands-a-go-go. Spare a dollar for the bucket-drumming street musicians, have drinks at the John Hancock Center’s Signature Lounge (95th floor, views galore) … or crown yourself King (or Queen) shop-a-lot.Accommodations in Magnificent Mile
Everyone’s an art critic. Especially round Superior and Franklin. Fall head over feet with art galleries here, with loft after loft lined with works by the USA’s prime talent. Mix your media at David Weinberg Photography, take a free art tour (usually 11:00 at 750 N. Franklin Street, Saturdays) or dine chic at chef Rick Bayliss’ fab Topolobampo.Accommodations in River North
Boom - you’ve found the fabled land of fun! Shop ‘til the credit stops along Magnificent Mile, a street with every commercial bell and whistle. Go on a kid-friendly jaunt to Navy Pier for fun rides and thrills on the giant Ferris wheel, or just walk around the Water Tower, a listed building that’s a stark contrast to the skyscrapers around it.Accommodations in Near North Side
Lincoln Park – historic, conservative and thriving. Home to Ivy League alumni and ladies lovingly referred to as ‘Trixies’, it’s a hubbub of activity day ‘n night. Find a foodie scene for any budget (try “Wiener Circle” for hot-dogs, Chicago style), stroll-worthy Lincoln Park Conservatory for orchids galore, and shows at the Steppenwolf Theatre.Accommodations in Lincoln Park
Get ready to lick your lips. Wicker Park packs in pancake joints, pizzerias and patio bars galore. Start the day with Irazu’s famous oatmeal shake, or try raspberry-and-Oreo flapjacks at Bongo Room. Stroll past the Victorian mansions of Hoyne Street, a.k.a “Beer Baron Row”, then sample trendy craft ales and thin-crust pizza at Piece Brewery.Accommodations in Wicker Park
Wealth meets privilege on the Upper East Side! Come here to stroll, unless you’re one of the lucky few buying in one of the USA’s most elite zip codes. You’ll see mansions in a litany of styles from Norman Gothic to Tudor. Michelin-star eateries abound. The area’s flanked by Lake Michigan and Oak Street (for all your spa and couture needs).Accommodations in Gold Coast
Socialite Stephanie says good food and good friends are the keys to happiness.
Afternoon Tea at the historic Drake hotel is the perfect excuse to get dressed up and enjoy some close company in a classy atmosphere. I highly recommend the finger sandwich selection – it’s so cute and delicious! Be sure to make reservations, otherwise you don’t stand a chance of getting a seat.Accommodations nearby
After 2 years, David is certain Chicago’s best spots are on the coast ofLake Michigan.
North Avenue Beach is a favourite local hangout, the perfect spot for a walk along the beach or to relax by the waves. There are also tons of activities – rent a jet ski, jump into a game of sand volleyball or give paddle boarding a try.Accommodations nearby
4 years in, Sanja has become a certified foodie who loves Chicago’s diverse dining options.
You’ll find me at the Green City Market on Saturday mornings during the summer. Check out this farmers' market for some fresh organic fruit and veg, and other speciality items. My favourites are the tinned beetroot from Bushel & Peck's and the croissants at Bennison's Bakery.Accommodations nearby
Tori is a laidback adventurer who seeks out quiet retreats in the urban jungle.
If you want to enjoy a picnic with an iconic view of the city in the background, head to the stretch of greenery between the Adler Planetarium and the Shedd Aquarium. Sprawl out and bask in the breeze coming off the lake. Hop on the ‘L’ to dodge the traffic congestions in this area!Accommodations nearby
For 10 years, Veronica has been biking to Chicago’s best kept secrets.
There are no hit-or-miss productions at the Steppenwolf Theatre. Each performance is compelling and powerful, and you’ll witness ground-breaking productions like ‘Grapes of Wrath’ and ‘August: Osage County’. This Tony Award-winning theatre is driven by artists who pursue on-stage innovation.Accommodations nearby
From lounging on the shore to partying on rooftop bars, Patrick’s 8 years in Chicago have been a blast.
Hop on a Chicago’s First Lady Architecture Tour to see all of Chicago’s architectural wonders. These riverboats run between April and November and will take you all around the city while your tour guide explains all the sights. Grab a drink from the full-service bar on board and take in some of the city’s best sights.Accommodations nearby
An outdoor enthusiast at heart, Matt still appreciates an exceptional cocktail and good food.
Al Capone and his mobsters once made their lair in the Green Mill Cocktail Lounge – today, it’s the best place to hear Chicago’s famous jazz music. The music goes late into the night and the bartenders serve legendary cocktails. Beneath the floor, Capone’s underground tunnel network still exists…Accommodations nearby
For 3 years, Michelle's motto ‘just go with it’ has taken her to Chicago’s most unique places.
If you want to beat the swarms of tourist shoppers on Magnificent Mile, head over to State Street. You’ll find similar upscale boutiques and luxury retailers minus the crowds. Don’t miss the Great Clocks and mosaic Tiffany Ceiling at the Marshall Field and Company Building.Accommodations nearby
Christina’s 2 years in Chicago have seen some epic shopping sprees at the most stylish shops.
I’m constantly on the lookout for unique styles that mesh with my unique personality. The Fashion Outlets of Chicago has incredible deals on loads of designer clothing. It’s located near O’Hare International Airport away from all the touristy areas. The Coach outlet has amazing deals on leather!Accommodations nearby
Ron has lived all over the US, but he’s convinced sweet home Chicago is the best.
Southport Lanes is the quintessential ‘neighbourhood bar’ with 4 vintage bowling lanes for some added excitement. Craft beer lovers will rave about the diverse selection of local Chicagoland brews and other brews from across the globe. You have to try the ‘Trendy’ – one of Chicago’s best burgers!Accommodations nearby
After 8 years of fast-paced life in Chicago, Jerome appreciates the city’s hidden gems the most.
I love this park! It was once a railway yard that has since been converted into a riverside community centre and children's playground. Hire a kayak nearby and admire the Chinese décor from the river. The best part about this park is the spectacular views of the Chicago skyline.Accommodations nearby
Booking.com asked travelers...What did you discover about the museums in Chicago that wasn't in the guidebooks?
In retrospect should have bought one of those "fast passes" after Willis tower, fine art museum, field museum, shedd aquarium, etc- would save money if you are going to all of them.See all 28 answers
Booking.com asked travelers...Where should people go if they don't want to eat in a tourist trap?
Google tapas restaurants in the area. They are all delicious and can always seat you the moment you walk in.See all 18 answers
Booking.com asked travelers...How can you enjoy the sights in Chicago while avoiding the crowds?
If your able to travel during the week it was much less busy and we hardly waited in any lines for anythingSee all 24 answers
Booking.com asked travelers...Is there more to shopping in Chicago than just brand-name stores?
United Arab Emirates
Yes! There are indie retailers a bit outside downtown and they are worth visiting.See all 13 answers
Booking.com asked travelers...Which fine art museums should a first-time visitor to Chicago start with?
United States of America
The Art Institute of ChicagoSee all 59 answers
Booking.com asked travelers...Describe what other people like you would like about shopping in Chicago.
Variety of stores.See all 19 answers
Booking.com asked travelers...What's the secret to sampling all the diverse food Chicago has to offer?
Visit oftenSee all 13 answers
Booking.com asked travelers...Did the theater performances in Chicago live up to their reputation?
United States of America
definitelySee all 16 answers
Chicago O'Hare International Airport is the city’s main airport. The best way to reach the city centre is by taking the CTA ‘L’ Train. Follow the signs in your terminal to reach the station. Purchase your fare (about USD 5) at the blue Ventra Vending Machines. The Blue Line runs 24 hours and takes you to the city centre in 40-45 minutes. Taxis cost around USD 35 and line up outside the terminal along the lower-level kerb. It’s at least 45 minutes’ ride to the city centre.
Chicago Midway International Airport is 18 kilometres from the city centre. The best connection to the centre is provided by the CTA ‘L’ Orange Line Trains (leaving every 10 minutes from 04:30–01:00, 7 days) which take around 25 minutes. Follow the signs in your terminal to the train station. Blue Ventra Vending Machines sell tickets for USD 2.25. Taxis line up outside each terminal and take around 25-30 minutes to reach the city centre, costing about USD 30.
The CTA elevated ‘L’ trains are the best way to zip around Chicago. ‘L’ stations are located all over the city centre designated by signs with names and line colour. Purchase fare cards inside at the blue Ventra Vending Machines. Single-ride tickets cost USD 3 and full day tickets are USD 10. Each train line is designated by colour and runs on a different schedule, but the Red and Blue Lines operate 24/7. Touch your ticket to the platform’s gate to pass through.
Metra trains are the easiest way to travel to and from the suburbs. There are multiple stations in the city centre clearly designated by a sign. Tickets can be purchased in the station from a ticketing assistant and cost between USD 3.50 and USD 10.50. You can also buy tickets on the train, but beware – a fee of USD 3 will be added to your total if a ticketing assistant was actually on duty when you passed through the station. Check online for operating hours.
The CTA bus system is best used to access places between the major stops on the ‘L’ train. Bus stops are located 1 or 2 blocks apart and clearly designated by a ‘cta bus stop’ sign – stand near the sign so the driver sees you. You can pay your fare with exact change when you board, otherwise buy Ventra fare cards from local retailers or the blue machines in ‘L’ stations (USD 2 for a single ride or USD 10 for a day pass). Check online for your route’s operating hours.
Taxis are an expensive option, but can easily be hailed from anywhere in the city. Yellow Cab is the most popular Chicago taxi – you can request a ride online or download the 'Curb' app for your smartphone. There is a fixed rate of USD 3.25 per ride and additional fees are tacked on for time and distance travelled. A simple journey can become an expensive endeavour. Tips are also encouraged for exceptional service.
Driving in Chicago can be a nightmare. Rush hour (07:00–09:00 and 17:00–19:00) creates massive gridlocks that can exponentially delay your journey. If you must drive, car rental is easy at either major airport. Drivers with an international licence or permit can easily rent cars with a valid credit card. Beware – use of handheld devices (including mobile phones) while driving is illegal and punishable by fine. Parking becomes scarce and expensive nearer to the city centre.
We've negotiated with thousands of hotels to get the very best deals. We call them Secret Deals and they only last for a limited time.
You can get these deals for free by subscribing to our newsletters. You can even choose your favorite destinations to receive personalized deals.
Get started now by entering your email address. We'll instantly send you a link to our Deal Finder!
Don't worry – your email address is safe with us. We'll never share your private information and you can unsubscribe at any time.
We'll send you a link to download the app directly from your mobile or tablet
Booking.com is part of The Priceline Group, the world leader in online travel & related services.
We have more than 70 million property reviews, and they're all from real, verified guests.
The only way to leave a review is to first make a booking. That's how we know our reviews come from real guests who have stayed at the property.
When guests stay at the property, they check out how quiet the room is, how friendly the staff is, and more.
After their trip, guests tell us about their stay. We check for naughty words and verify the authenticity of all guest reviews before adding them to our site.
If you booked through us and want to leave a review, please sign in first.