The Ultimate Weekend Trip to Chicago
Chicago is truly the gem of the Midwest. Perched on the scenic shores of Lake Michigan, the Windy City is a stunning metropolis that seems a bit out of place amongst the Great Plains. From world-renowned architecture to an iconic food scene, Chicago feels closer to New York than to Illinois (but don’t let the locals catch you making that comparison). Although there’s a seemingly endless variety of things to discover here, you can absolutely see the best of Chicago on a weekend trip. This guide will cover all the essentials for planning your Chicago getaway – including the best things to do, the best time to visit, and how to get around the city.
This is your guide to a weekend trip to Chicago, Illinois.
Getting to Chicago
There are two major international airports in Chicago – O’Hare (ORH) and Midway (MDW). O’Hare is the largest, but both are international airports.
To get from the airport to downtown Chicago, I highly recommend taking the ‘L’ (Chicago’s public transport system). It will be much more affordable than a taxi or Uber, and it’s also pretty convenient. Just follow the signs in the airport to the CTA train and purchase a ticket from the kiosks at the entrance. You can also use the ‘tap to pay’ function on your phone to get through the barrier rather than purchasing a physical ticket. There’s just one line operating to and from each airport (the blue line for O’Hare and the orange line for Midway), so you don’t have to worry about getting on the wrong train – they’re all the same when leaving the airport.
Getting Around Chicago
If you can avoid it, I do not recommend renting a car while in Chicago. You’ll spend way too much time in traffic and trying to find parking. Luckily, Chicago is pretty easy to navigate by other means, so a car is completely unnecessary for a weekend trip.
The “L”
The “L” (short for “elevated”) is Chicago’s train system and is the main source of public transportation. The (mostly) above-ground train (there’s one line that runs underground like a traditional subway) is an affordable and convenient way to get around the city.
NAVIGATION TIP: I love the app Citymapper for navigating public transport in a new city. It will help you know what line to take, where the nearest station is, and what stop to get off at.
Walk
As long as you’ve got good weather (i.e. it’s not mid-winter), walking is one of the best ways to explore Chicago. The city is relatively flat with paved sidewalks, so you’ll see plenty of locals and tourists alike getting around on foot.
Rideshare
If the “L” doesn’t have a stop near where you’re headed, and walking isn’t feasible, rideshare is probably the way to go. Uber and Lyft both operate in Chicago and are widely available.
Is Chicago Safe?
From the days of Al Capone to modern crime statistics, Chicago has, unfortunately, garnered a bit of a notorious reputation. While I can’t deny the stats, I can say from experience that I have yet to feel or witness anything unsafe throughout my (many) visits to Chicago. The areas that you’ll be exploring as a tourist are generally very safe overall. That being said, use common street smarts, travel with a companion (if possible), and keep valuables in a safe place.
Riding the L is also generally safe, but if you’ll be out past midnight consider using Lyft or Uber instead. If you’re alone at night and need to take the L, sit in the front car nearest the conductor.
Best Time to Visit Chicago
SUMMER
June through August are the warmest and most popular times to visit Chicago. This is when you’ll see the highest hotel prices and largest crowds at popular tourist destinations like Millenium Park. Chicago really comes alive in the summer, but keep in mind that the heat and humidity can get overwhelming. For cooler weather and fewer crowds, aim to visit in early June.
AUTUMN
Summer gets all the hype, but I think autumn is really the best time to see Chicago. The weather is generally comfortable, there are fewer crowds, and the colors (particularly around Grant Park) are lovely.
WINTER
Christmastime in Chicago is magical with lights, festivals, and decorations all throughout the city. Bonus: winter is the low season in Chicago, so you’ll see fewer crowds and lower prices at hotels. Weather in December can be a bit of a gamble, but I think it’s worth it if you’re looking for a Christmas getaway. The rest of winter, however, can be downright brutal. With heavy winds, unbearably cold temperatures, and plenty of snow, avoid visiting from January through March.
SPRING
Spring is short but gorgeous in Chicago. Tulips bloom along Michigan Avenue and parks burst with cherry blossoms. Expect a chance of rain, and don’t be surprised if you experience some unseasonably cold temps (particularly in early April).
The Windy City
Nicknamed the Windy City, a lot of visitors think the weather in Chicago must be…well, windy.
While, yes, Chicago does get windy at times, the nickname doesn’t have anything to do with the weather. The moniker instead comes from New York and Cincinnati journalists who editorialized that Chicago politicians were “full of hot air” or “full of wind”.
Where to Stay in Chicago
There are countless hotel options throughout Chicago for all budgets. While I often use sites like AirBnB or Vrbo when traveling, I always opt for a hotel when visiting Chicago. They tend to be much more conveniently located near attractions and L stations. These are a few of the best areas to book your stay.
The Loop
Centrally located, this is the most popular and most convenient place to stay in Chicago – especially if you’re a first-time visitor. You’ll be within walking distance of Millenium Park, the Magnificent Mile, the Theater District, the Riverwalk, and more.
River North & Streeterville
This is a great neighborhood to stay in if you’re looking for a more budget-friendly option that’s still close to the action. With fewer L stations, the location is a little less convenient than The Loop, but it’s still centrally located. River North is closer to great restaurants, while Streeterville will put you next to Lake Michigan, Navy Pier, and the Magnificent Mile.
West Loop
If you’re coming to Chicago solely to eat, station yourself in the West Loop. This is where you’ll find a lot of Chicago’s most trendy restaurants. It’s a little removed from the major Chicago attractions, so this neighborhood is better if you’ve already visited the city before.
Gold Coast or Old Town
These neighborhoods are also better for those who have visited Chicago before and are looking to explore beyond the main highlights. Both are on the north end of the city near the Lincoln Park Zoo, but each has its own qualities. Gold Coast is an affluent neighborhood brimming with historic mansions, designer boutiques, and acclaimed restaurants. Old Town is a bit more lively with restaurants, comedy clubs, and neighborhood haunts.
Second City
The city so nice, they built it twice.
Another common nickname for Chicago with misunderstood origins is Second City. No, it doesn’t mean that Chicago is “second best” (though many New Yorkers might like to think that’s the case). It got this name because the city has been built twice. After the Great Chicago Fire, the city was rebuilt atop the ruins to become the Chicago that you know today – the Second City.
Best Things to Do on a Weekend Trip to Chicago
Take an Architecture Cruise
The best way to see the renowned architecture of Chicago is by boat. In fact, taking an architecture cruise is the number one thing my local friends recommend for visitors. There are a number of cruise options, but my favorite is the original from Wendella Boat Tours. It’s a great way to learn more about the city as well! I promise you’ll find this cruise entertaining even if you’re not an architecture buff.
Enjoy the scenic Chicago Riverwalk
If you can’t enjoy the river views by boat (or even if you can), then certainly check out the Chicago Riverwalk. The 1.25-mile walkway will take you all the way from the city center to the Lake Michigan waterfront. Along the way, you’ll find restaurants with riverside patios, public art, and even a museum all about the Chicago River and its movable bridges.
Lakefront Trail & Milton Lee Olive Park
The only thing better than the view of the river in Chicago is the view of Lake Michigan. If you’ve never visited one of the Great Lakes before, be prepared to be stunned. The lake is so vast, standing on the coastline you could almost swear you were at the ocean. Lakefront Trail along the shore is the perfect spot for a walk, and Milton Lee Olive Park offers some gorgeous views of both the city skyline and Lake Michigan.
North Avenue Beach: If you’re able to venture out a little further, this beach is another gorgeous option for visiting the lakefront. This is a popular spot for photos, and it’s easy to see why. The views of the city skyline across the lake are particularly beautiful around sunset.
Sample some of Chicago’s famous foods
When you think of Chicago, what do you think of? If “pizza” wasn’t one of the first words to come to mind, we might not be talking about the same city. Chicago is home to a number of delicious dishes, including its famed pizza, and you should definitely sample as many things as you can while you’re here. These are a few to put on your list:
- Deep-dish pizza from Pequod’s Pizza (if you’re vegan, check out Gino’s East or Kitchen 17 instead).
- Tavern-style pizza (the style typically preferred by locals) from Vito & Nick’s.
- Italian Beef from Al’s Italian Beef.
- A Chicago dog with everything (I like Devil Dawgs), and don’t you dare order ketchup.
- A burger from Au Cheval (or the more casual Small Cheval).
- Chicago-style popcorn from Garrett’s.
Visit “The Bean” at Millenium Park
No first-time visit to Chicago is complete without a visit to Cloud Gate, aka “The Bean”. The reflective art installation is beautiful against the backdrop of the city. Once you’ve snapped your share of photos, take some time to explore the rest of Millenium Park and the connecting parks as well.
The Bean is one of the top destinations in Chicago, so if you’re looking to avoid crowds, get there early or visit in the winter (brrr).
See Buckingham Fountain in Grant Park
Not far from Millenium Park is Grant Park, and the crown jewel here is the stunning Buckingham Fountain. It’s huge! If you have a little more time during your weekend trip, definitely make a stop at the Art Institute of Chicago nearby as well.
This may seem obvious, but do note that if you visit during the winter the fountain won’t be running.
Enjoy stunning views from an observation deck
The Skydeck at the Willis Tower (formerly known as the Sears Tower) is one of the most iconic ways to see the city from above. On a clear day, you can see up to four states, and the glass floor enables you to see straight down from the top of the tower.
While the Willis Tower is the most popular, I love the 360° Chicago views from the Hancock Tower near the waterfront. The observation deck offers 360° views of the city (skip the extra cost for the “Tilt” option that tilts you outward over Michigan Avenue – it’s really not worth it).
HOT TIP: Skip the expensive entrance fee at the Hancock Tower and head up to The Signature Lounge on the 96th floor instead. You’ll have to buy a drink, but it’ll be a fraction of the price of visiting the observation deck (and it’s actually a floor higher than the observation deck).
If rooftop bars are more your speed, Chicago has spectacular options. Cindy’s near Millenium Park is probably the most renowned – both for the menu and the views. Another beautiful option is the rooftop at London House along the river. Both book up quickly though, so be sure to grab reservations in advance.
Take a ride at Navy Pier
Truthfully, Navy Pier is one of my least favorite places to visit in Chicago (it’s just ultra touristy and always crowded when the weather’s nice). If it’s your first visit to Chicago though, you have to see the Ferris wheel on the pier – it’s just so iconic. Better yet, ride the Ferris wheel! It’s a lovely and relaxing way to take in the city.
Go window shopping on the Magnificent Mile
The stretch of Michigan Avenue known as the Magnificent Mile is Chicago’s premier commercial district. It’s home to upscale shops, posh hotels, beautiful old buildings, and even the largest Starbucks Roastery in the world (it’s four floors plus a rooftop).
Take a walk around Gold Coast
The quiet, tree-lined streets of Gold Coast make up Chicago’s most exclusive neighborhood. Here you’ll find multi-million dollar brownstones alongside historic mansions (including the original Playboy mansion). It’s a beautiful place to grab a coffee and go for a quiet stroll.
Visit some of Chicago’s best breweries
Chicago has a burgeoning micro-brewery scene. The most well-known is probably Goose Island which has two locations in Chicago. There are great breweries all throughout the city, but the West Loop is probably the best neighborhood for brewery hopping.
Catch a Comedy Show
The comedy scene in Chicago is legendary. It’s home to The Second City, the iconic improv venue that brought us stars like Tina Fey, Steve Carrel, Chris Farley, Stephen Colbert, Tim Meadows, and countless others. Chicago is also the hometown of comedy greats like John Belushi, Bill Murray, and John Mulaney. As such, there are few things more memorable than catching a comedy show in Chicago during your weekend trip. Aside from the aforementioned Second City, other great spots include the historic Zanie’s and the famous Laugh Factory.
Discover Chicago’s Notorious Mobster Past
Thanks to the likes of Al Capone, Chicago’s history is irrevocably tied to prohibition-era mobsters. To learn all about it, join one of the many Chicago Gangster tours. If you’d rather skip the history lesson and just experience Chicago the way Capone did, make a stop at The Green Mill cocktail lounge for drinks and live jazz. The former speakeasy is well-known to have been frequented by Al Capone himself.
Whether you’re looking to eat your way through the city or to feast your eyes on some incredible scenery, Chicago has a lot to offer. A weekend trip to the Windy City will give you ample opportunity to discover the best of Chicago.
Have any questions about your upcoming trip to Chicago that I didn’t answer here? Let me know in the comments.
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