A Drinker’s Guide: How to Chug Like a Champ in Chicago

Discover the best Chicago drinks, bars, and nightlife tips. Plan your trip with cheap flights, great brews, and unforgettable nights.

Chicago is more than just deep-dish pizza, skyscrapers, and baseball—it’s also a city that takes pride in its drinks. From legendary beer halls and cozy cocktail lounges to rooftop bars with lake views, Chicago drinks culture is one of the best in the United States. If you’re planning a trip, you don’t want to miss out on exploring this side of the Windy City.

The good news? Getting here is easy with plenty of affordable flight options. You can book flights from Detroit to Chicago with real-time deals or even grab cheap round-trip flights from Denver to Chicago depending on your schedule. Once you land, the city welcomes you with endless ways to sip, savor, and celebrate.

In this guide, we’ll walk you through the essentials—from local breweries and cocktail spots to must-try drinks, travel tips, and money-saving advice. Think of it as your ultimate handbook to exploring Chicago drinks like a pro.

Why Chicago is a City Built for Drink Lovers

Before diving into bar-hopping, it helps to know why Chicago drinks are such a big deal.

• Historic Brewing City: Chicago has been a beer hub since the 1800s. Local breweries like Goose Island started trends that spread nationwide.

• Diverse Neighborhoods: From upscale lounges in River North to dive bars in Logan Square, every area offers something unique.

• Cultural Influence: German, Irish, Polish, Mexican, and Italian immigrants brought their traditions, shaping today’s Chicago drinking culture.

• Events & Festivals: Beer fests, cocktail competitions, and summer block parties make Chicago one of the best cities to enjoy a drink outdoors.

Whether you’re flying in from the East Coast or the South, affordable options are available. For example, you can find lowest airfares from Atlanta to Chicago or check best flight deals from Dallas to Chicago and time your trip with a major festival.

Must-Try Chicago Drinks

Chicago has signature drinks you can’t leave without trying. Here are the highlights:

1. The Iconic Malört

Love it or hate it, Malört is Chicago’s rite of passage. This bitter liqueur has a strong flavor that locals joke about—but tourists proudly try at least once.

2. Old Style Beer

Once the official beer of Wrigley Field, Old Style is a simple lager but a local favorite. You’ll find it in almost every dive bar.

3. Chicago Handshake

This is the combination of Malört and an Old Style beer—ask for it by name and bartenders will know exactly what you mean.

4. Local Craft Beers

Chicago is home to dozens of breweries like Revolution, Half Acre, and Lagunitas. Each neighborhood has a taproom worth visiting.

5. Fancy Cocktails

For those who prefer something more upscale, Chicago’s mixology scene is world-class. Rooftop bars in the Loop serve creative cocktails with skyline views.

Flying in for a weekend? Don’t forget you can book cheap flight tickets from Cleveland to Chicago or even look at direct flights from Boston to Chicago for last-minute fun.

Best Neighborhoods for Chicago Drinks

Each part of Chicago offers a different drinking experience. Here’s where to go:

1. River North

Known for trendy cocktail lounges, rooftop bars, and dance clubs. Perfect for a dressed-up night out.

2. Logan Square

The heart of craft beer and indie cocktail bars. Casual, hipster-friendly, and full of hidden gems.

3. Wicker Park

Great mix of dive bars, live music venues, and creative cocktails. Popular with younger crowds.

4. Pilsen

A lively neighborhood where Mexican culture shines—sip on micheladas, tequila cocktails, and Mexican craft beers.

5. Lincoln Park

College-friendly vibes with affordable beer deals, sports bars, and casual hangouts.

Travel tip: Want to compare neighborhoods easily? You can compare flight tickets from Houston to Chicago or check affordable flights from Indianapolis to Chicago depending on where you’re traveling from.

Step-by-Step Guide: How to Explore Chicago Drinks Like a Local

Here’s a simple step-by-step plan to make the most of your Chicago drinks adventure:

Step 1: Book Your Flights Early

Chicago is a busy city year-round. Booking early means more money left for drinks. Look out for discounts on flights from Orlando to Chicago or book flight tickets from Philadelphia to Chicago at lower prices.

Step 2: Pick Your Stay Wisely

Stay near neighborhoods like River North or Logan Square if drinks and nightlife are your focus. This way, you’ll save time and money on transportation.

Step 3: Start with Breweries

Spend your first afternoon exploring breweries. Try flights (small samples of multiple beers) before committing to a pint.

Step 4: Do the Cocktail Circuit

After breweries, explore rooftop lounges for cocktails. Don’t miss bars like LondonHouse or Cindy’s.

Step 5: End at a Dive Bar

Finish your night at a local dive bar with Old Style beer and maybe a Malört shot.

Tips for Saving Money on Chicago Drinks

Drinking in Chicago can get expensive, but there are ways to keep your wallet happy:

• Happy Hours: Many bars run early evening deals.

• Beer Buckets: Great for groups at sports bars.

• Neighborhood Specials: Logan Square and Lincoln Park often have $3–$5 beer nights.

• Flights & Travel: Save before you arrive by booking smart. For example, look for cheapest flight tickets from Richmond to Chicago or round-trip flights from Miami to Chicago.

Festivals and Events for Drink Lovers

If you time your trip right, you can join amazing drink-centered events:

• Chicago Beer Festival (Spring): Hosted at the Field Museum with dozens of breweries.

• Craft Beer Week (May): Breweries all over the city release special batches.

• Chicago Gourmet (Fall): Food and drink event with celebrity chefs and mixologists.

• Summer Street Fests: Neighborhood block parties with outdoor beer tents.

Festival travel tip: You can book flights to Chicago easily or even catch last-minute flights to Chicago if you’re spontaneous.

Pairing Drinks with Chicago Food

What’s a drink without food? Chicago pairs its beverages with amazing eats:

• Deep-Dish Pizza + Beer → A must-do combination.

• Italian Beef + Old Style Beer → Classic Chicago pairing.

• Street Tacos + Margarita → Try in Pilsen.

• Hot Dogs + Craft Beer → Found everywhere, especially near ballparks.

Need to plan ahead? There are flights from Charlotte to Chicago and cheap round-trip flights from Nashville to Chicago so you can align your visit with food festivals, too.

Nightlife Beyond Drinks

While Chicago drinks are the highlight, nightlife offers much more:

• Live Music Venues: From blues bars to jazz clubs, Chicago has deep roots in live music.

• Comedy Clubs: Laugh Factory and Second City are perfect after a few drinks.

• Sports Bars: Watch the Cubs, Bears, or Bulls while sipping a pint.

• Rooftop Views: Many hotels and bars feature skyline views worth the visit alone.

If you’re flying in late, you’ll still find options since the city doesn’t sleep. Look for airlines flying from California to Chicago or best flight deals from Washington to Chicago for convenient scheduling.

Safety Tips While Enjoying Chicago Drinks

Drinking responsibly is key:

• Use rideshare apps to get home safely.

• Drink water between rounds.

• Keep cash handy for dive bars (not all accept cards).

• Don’t mix too much if you’re trying Malört—it’s strong!

Travel safe by planning ahead. For instance, flight reservations from Colorado to Chicago or cheapest airfares to Chicago can make sure you’re well-prepared before arriving.

Conclusion: Raise a Glass to Chicago Drinks

Chicago isn’t just a city you visit—it’s a city you drink with. From breweries and cocktails to iconic shots like Malört, every bar tells a story. Whether you’re here for a weekend or a week, the world of Chicago drinks is ready to welcome you.

Plan smart, save money on flights, and drink like a local. You can book cheap flights to Chicago today and start planning your ultimate nightlife adventure. So, grab your passport, pack your appetite, and raise your glass—the Windy City is waiting for you!