Top Places to Drink in Chicago

Chicago is a city that understands the joy of a good drink. Whether you land after a long flight or wait for your hotel check-in, there’s always a great spot nearby to relax with a glass in hand. If you’re using transport services to reach your hotel, you’re already off to a convenient start. Now, you can raise a glass without straying too far from your path.

From O’Hare to the City: A Toast Along the Way

O’Hare International Airport sits about 17 miles northwest of downtown Chicago. If your ride takes you into the city’s heart, you’ll pass through neighborhoods with low-key gems. One of the earliest stops you might consider is in the Jefferson Park or Logan Square areas. They have a growing number of taverns serving craft and classic selections. Many places pride themselves on friendly service and a laid-back vibe, perfect for travelers who want to ease into city life.

As you get closer to downtown, the West Loop offers a nice mix of modern and industrial-style bars that are lively but not overwhelming. This area is especially good if you appreciate a place where the menu is as thoughtful as the drink list.

Midway Arrivals: South Side Sips

Flying into Midway and catching a shuttle? The route to the city center can be surprisingly rich. The neighborhoods near Midway, like Garfield Ridge or Bridgeport, might not always show up on tourist maps, but they’re home to corner bars and lounges that reflect Chicago’s proud working-class roots.

Many of these spots serve generous pours at fair prices, with plenty of charm and no pretension. You’ll often find bartenders who’ve worked there for decades, always ready with a story or a recommendation for your next stop. If your car route skirts along the southern edge of the Loop, there are also rooftop lounges that offer pretty views!

Downtown Drops: Within Walking Distance

Once your airport shuttle drops you at your hotel, downtown Chicago opens up like a well-organized bar cart. The Loop, River North, and Streeterville areas are packed with watering holes that range from upscale to unassuming. The beauty here is in the variety: whether you’re in the mood for a quiet bourbon in a dim corner or a cold lager at a bustling bar with sports on every screen, you’ll find it within a few blocks.

Hotels themselves often host solid options, too. While hotel bars sometimes get a bad rap, Chicago’s scene does them well. These in-house lounges feel more like neighborhood staples than temporary pit stops. They’re ideal for when you just want to grab a drink without wandering too far.

After the First Sip: Making the Most of Your Stay

Once you’ve settled in, you might be ready to explore deeper. Chicago’s neighborhoods like Pilsen, Wicker Park, Andersonville, and Hyde Park each offer their own drinking culture. But your first hours, between landing and unpacking, can already offer a taste of what the city does best: blending history, community, and good spirits into one smooth experience. If you’re looking for a Chicago Airport Shuttle to Hotel here, you just need to contact All American Limousine!

With shuttle services taking care of the route and the city’s hospitality doing the rest, finding a good drink in Chicago becomes less about planning and timing. And in this city, it’s always a good time for one. Step off, drop your bags, and raise your glass. You’ve just arrived in one of the greatest drinking cities in the world, which is ready to welcome you with open arms.