Where to stay in Chicago

A couple capture the scene on a Chicago street

Made up of a long list of neighborhoods and districts each offering something different, deciding where to stay in Chicago can be a bit of a headache, especially if you’re a first-time visitor to the city.

Whatever you’re looking for out of a leisure trip to the windy city, our pick of the best areas of Chicago to stay is sure to be a help!

The Loop

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Enclosed by the Chicago River to one side and Grant Park to the other, the Loop is probably the best place to stay in Chicago for those new to the city since its streets include the central business district and many of the city’s top attractions, including the Willis Tower’s Skydeck observation level and the Art Institute of Chicago. It takes its name from the elevated railway which has looped around it since the Great Fire of 1871.

Synonymous to most with the downtown area, it’s also one of the commercial hubs of the city. Being at the heart of the action (Route 66 starts here too), there’s no shortage of hotels either.

Predominantly populated by luxury stays – the Hyatts and Radisson Blus of this world – budget travelers will likely find themselves looking at more affordable neighborhoods nearby, such as Lincoln Park. However, the Loop does it have a good quantity of backpacker hostels for those just looking for a central place to lay their head at the end of a long day of sightseeing.

Streeterville

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Immediately north of the Loop on the shores of Lake Michigan, the Streeterville neighborhood is still close enough to downtown to be a worthwhile base and is a good pick for solo travelers and visiting couples.

Known to be a very safe neighborhood in Chicago for visitors, it has some similarities to its southern counterpart. Gleaming tower blocks line the Magnificent Mile (a part of North Michigan Avenue), containing roughly 450 stores as well as the famed 875 North Michigan Avenue (John Hancock Center).

Its southern extent stretches out into Lake Michigan thanks to the 50 acre Navy Pier. Its rides include Centennial Wheel, which replicates the world’s first Ferris Wheel, built in 1893 for the World’s Fair.

Lincoln Park

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A little further out, but linked to the rest of the city by a number of metro stations and lines, Lincoln Park is one of the largest and most affluent districts in Chicago’s North Side. It is popular with young families and urban professionals, ensuring it feels fresh and ever changing.

Named after the city’s largest park, which sits beside Lake Michigan for an uninterrupted seven mile run, the area is one of the best parts of Chicago for those on a budget. Attractions include the 32,000 creatures which call Lincoln Park Zoo their home, as well as Chicago History Museum, the first port of call for anyone interested in discovering how Chicago became one of the world’s leading cities.

Lincoln Park also contains the northern half of Old Town, where buildings remain low to the ground – at least by Chicago standards – to create a homely feel. This is where you’ll find the Second City Theater, the previous stomping ground of everyone from Tina Fey to John Belushi.

River North

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It may not have the lake shore, but River North does have a reputation as the coolest place to stay in Chicago. Separated from Streeterville by the Magnificent Mile, River North oozes stylishness and perhaps contradiction too – it has more galleries than anywhere outside of Manhattan, but is also known for its nightlife. For this, you should head to Hubbard Street.

The banks of the Chicago River have to be the top place for a stroll in the area, whilst landmark buildings to look out for include the Wrigley Building and the monumental behemoth of a structure known as Merchandise Mart, whose exterior façade becomes the world’s largest projector screen for a few months of each year.

A good range of restaurants, many with riverside terraces, means you’re unlikely to go hungry for long.

West Loop

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That said, foodies should stake their claim to accommodation in West Loop, which – that’s right – is west of the Loop.

Occasionally also known as the Near West Side, West Loop shines from a gastronomic perspective, with Greektown and Little Italy just two destinations you should be aware of thanks to the twentieth century’s influx of immigrants into this former industrial port area.

Randolph Street is otherwise known as Restaurant Row for good reason, but for sumptuous food without any pretension head to the French Market tucked inside Ogilvie train station. Its 30+ independent vendors make it one of the best spots in the city for fresh ingredients as well as mouthwatering dishes from sushi to empanadas. Seating is available.

Wicker Park

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Well-to-do Wicker Park is growing in confidence when it comes to where to stay in Chicago. Northwest of West Loop and centered around the Damen metro stop, this neighborhood has the sort of self-assurance which usually leads to great things. And Wicker Park is no exception to this rule.

A charmingly informal blend of eclectically-stocked clothing stores, groundbreaking restaurants and we-just-have-to-stop-there bakeries, Wicker Park is also pretty hot when it comes to night spots, with a wealth of live music venues all vying to be the place to head.

With median house prices of $550,000 it can never really be called hipster, but that’s certainly the vibe it gives off.

Budgeting for trips to Chicago

Finding where to stay in Chicago that’s right for you comes down to a balance of location, feel and price. The best neighborhoods in Chicago for visitors are generally those in and around the downtown area, although the closer you are to the Loop, the higher the per night cost you’re probably looking at.

When it comes to attraction admission, you can make incredible savings simply by opting to travel with Go City. Our pre-pay passes take all the mystery out of budgeting for trips to Chicago whilst providing you with great savings on many of the city’s top attractions.

Ian Packham
Go City Travel Expert

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Things to do in Bucktown, Chicago

Chicago's your vacation destination, is it? Excellent. May we interest you in one of its many districts, Bucktown? If you don't know about it, don't worry. Sit down, be quiet, and we'll tell you all about the best things to do in Bucktown, Chicago. Including: Bizarre sports Rundown exploration Theatres Live music Restaurants and more! Get Whirly Let's get this Bucktown show on the road, with something slightly different. Whether you're a fan of sports or not, you might just love this new kid on the sporting block. What do you get if you combine lacrosse, hockey, basketball, and bumper cars? WhirlyBall is what you get. This crazy, made-up pastime combines elements of all of these into one awesome game. Get together a few friends, grab a few delicious craft beers at the bar, and try your luck on the WhirlyBall court. There are three of them onsite, along with bowling lanes, laser tag, and the aforementioned bar. Careful if you go to WhirlyBall at the start of your vacation. You may very well never go anywhere else. You're the Explorer Want to touch some grass, experience great views of the Chicago skyline, and explore some abandoned architecture reclaimed by nature? Then you'll want to check out The 606. This abandoned railway line worms its way through many of Chicago's districts, including Bucktown. So, feel free to get on at any point, explore a bit, and then 'hop off' at a different location and look around. If that wasn't enough, you'll also find a myriad of events going on there, from bake sales to outdoor yoga. Whether you saddle up or use your feet, you've got quite the adventure ahead of you. So, what are you waiting for? Showtime! How about a little theatre to dramatize your vacation? Bucktown's got a bunch of performance venues that'll happily accommodate your bum in one of their seats. Gorilla Tango Theatre is a community-led bunch that ensure every penny they make goes back into further productions. That includes sets, props, and other items that might otherwise be wasted. It sounds like a tall order, but they've already produced over one thousand awesome shows with this business model, and they have no intention of stopping. This model also allows them to give exposure to local theatrical artists, ensuring the city's scene continues to thrive. So, if you want to see what sustainable theatre looks like, go check them out! Or, if you want to see American takes on tough European plays, give Trap Door Theatre a go. They use expressionism and absurdism to recontextualize well-known works, so you'll never see a performance quite like it! Having moved around the European scene, they've not settled in Chicago, where'll they'll happily blow your mind! Gigging Speaking of performance, why don't we throw some live music into the mix? Bucktown's got its fair share of concert venues. Hideout takes its name quite literally, as it can be hard to find without a map. However, those of you with the know-how to seek it out are in for a treat. It's in the heart of Bucktown's industrial area, but you'll find nothing but country within. With a host of regular country-rockers, as well as a variety of touring artists, you'll love listening to some bluegrass twangs will sipping cheap beer and tapping your cowboy boot. Switching gears a little, Subterranean is where you'll find Bucktown's alternative music scene. With regular rock, rap, and metal gigs going on throughout the year, as well as club nights every week, it's the hip-happeningest place around. Is it a bird? Is it a plane? No, it's comics. Specifically, a great comic shop with countless issues of the best comics and graphics novels around! Challengers Comics + Conversation pride themselves on their expertise, as well as their ability to talk with their mouths. That means you can expect to get great advice on any comic or graphic novel you're looking for, or recommendations for ones you've never heard of. All that, and just some pleasant conversation to boot. Brilliant. Eats Let's move on to food now, as you're doubtless hungry after all that sweet information we've given you. As you'd expect, Bucktown has some great eateries for you to eat in, just like the rest of Chi-Town. Here are our faves! The Bristol twists American classics with a New American style. They make everything fresh, right in the kitchen, so you can expect great-tasting food all day, every day. Why not order a pasta dish with, yes, freshly made pasta, and pair it with a lovely cocktail from their menu? Want to try some Central American cuisine you may never have had before? Get Costa Rican at Irazu, and try some traditional treats in this delightful spot. Just bring your own booze if you want to drink. Don't worry; they're okay with it. Got a sweet tooth? Never you worry, friend. Margie's Candies is here for you. Inside, you'll find ice cream, sweet treats, and milkshakes, all hand-made with care. A delightful stop on your Bucktown tour if you just need a sweet fix to get you through the day. Drinks Let's end this list with a drink or two. If you're looking for a night out, Bucktown's got you covered. Here are our picks for the hottest spots to wet your whistle. Part performance venue, part drinking establishment, Gallery Cabaret has a bar rammed full of beers, spirits, and everything in between. It pairs all that with a wealth of live entertainment, from jazz music, open mic nights, and blues bands all the way to bingo. It could be the perfect night out for you, as long as you like the entertainment! Or, if you'd prefer a more standard bar experience, then check out The Map Room. This explorer-themed establishment has a wide variety of drink options from all over the globe, which is appropriate, really. Step inside, admire the decor, and then stare in awe at the massive variety of craft beers on offer. It's enough to make your head spin. And that's our list of the best things to do in Bucktown, Chicago!
Dom Bewley

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