While each of our guides aims to offer simple advice in a format that's easy to navigate and share, we recognize that not all travel enthusiasts can translate that information into an actionable plan. We also understand that not everyone has the bandwidth to take on the details of planning a trip. If you would like to purchase a turnkey itinerary that outlines a long weekend in Chicago, click here for a family friendly adventure and here for a pre-planned girls weekend away.

Where?

Chitown, Illinois

I do my best to visit Chicago annually for a quick weekend getaway. I typically stay in the downtown area, but also head north to explore Old Town, Lincoln Park, and Wrigleyville. 

When to go?

My favorite time to visit is in late August or early September, hoping to miss some of the summer crowds. However, if you go in the winter, the city is even less crowded. While planning your trip, be sure to check out any big events that might be happening. I once unknowingly visited during Lollapalooza and the entire downtown, including the museums, were a madhouse.

Rtip: While there are always outdoor concerts in the park during the summer, get your hands on the Chicago Reader either before going or once you arrive. They always have a pretty comprehensive list of current galleries, fun exhibitions and live music that might catch your eye.

How to get there?

The best way to get to Chicago is by flying into either O’Hare Airport or Midway Airport. O’Hare is the larger of the two airports and typically offers cheaper flights. Midway is a smaller airport, making it easier to get through, and it’s closer to downtown. From O’Hare you can take a 40 minute ride on the ‘L’ (the elevated train) or take your chances in traffic and grab a taxi or Uber into the city. Depending on the time of day, the ‘L’ might be faster. 

If you are thinking about driving to Chicago or renting a car there, don’t. I can’t stress this enough. Between traffic and parking fees, it’s not worth it. Once you’re in the city, you can get everywhere via the transit system, taxi or Uber, or renting a Divvy bicycle. The city has put a substantial amount of money into bike lanes and Divvy is quite affordable, at $15 for a three hour ride.

Rtip: When considering transportation in Chicago, the L” really connects you in the best way possible. Consider purchasing contact-less Ventra tickets from station vending machines to make life easy. Rides cost a flat rate irrespective of the destination and if you are staying for several days they offer passes that grant unlimitied rides.

Where did you stay?

Chicago is known for the variety of neighborhoods spread throughout the city. I recommend choosing where you stay based on location over anything else. My favorite place to stay is near The Art Institute of Chicago. This gives me proximity to Grant Park, shopping on Michigan Avenue, and walking to a Broadway show. The Palmer House, is a grand, historic Hilton property, charming but exceptionally renovated and in a great location, not to mention it’s newly erected indoor, heated pool and spa.

*See our Chicago Itineraries for additional stay recommendations.

What should we do?

There are four things that are a “must-do” every time I visit the city: The Art Institute of Chicago, shopping, seeing a Broadway show and hitting a Cubs game. 

Chicago has some of the best museums in the country but my top choices are always going to be  The Art Institute of Chicago, the Shedd Aquarium, and the Museum of Science and Industry. Key pieces to see at the Art Institute include Nighthawks by Edward Hopper, American Gothic by Grant Wood, and A Sunday Afternoon on the Island of La Grande by Jatte by Georges Seurat. Be sure to watch Ferris Bueller’s Day Off before visiting, to really get in the spirit. I also suggest purchasing tickets ahead of time to avoid the lines. 

The CIBC Theatre located on West Monroe Street is a sight to see! Built in 1906, it maintains its original fixtures, along with the original mosaic lobby floor. Be sure and walk around during intermission and take in the exquisite chandeliers. Also, do not purchase an “obstructed view” seat as these are located behind large columns and block the view.

Watching a Cubs game at Wrigley Field is a must-do, even if you are not a fan of baseball. The iconic baseball park is a great experience and almost any seat gives you a decent view of the game. Grab a famous Chicago hot dog and sit back to cheer on the Cubbies. If you attend during the day, be sure to wear sunscreen, and bring sunglasses and a ballcap.

Rent a Divvy bicycle and ride the Lakefront Trail to Chicago’s free outdoor zoo, Lincoln Park. During the summer the Architecture Boat Tours are a unique and fantastic way to see the city. If I was going to Chicago for the first time, I would highly recommend taking one of these tours on the first day of your visit, as it will give you insight into the city you are about to explore.

Rtip: Don’t be afraid to swim in lake Michigan. The water is safe and there are 25 beaches lakeside for you to explore, weather permitting. For more specific ways to take to the water, check out our itineraries.

What should we eat?

I’m not a foodie, but I can tell you about pizza. And what would a trip to Chicago be without enjoying a Chicago-style pizza? This deep dish of deliciousness can be found in almost every pizzeria across town. Throughout the years I’ve been to many of the pizzerias in the Windy City and my top vote is still Giordano’s. There might be a wait, but it’ll be worth it!

Other top-notch restaurants include Tzuco, an upscale Mexican restaurant with a superb brunch. If you’re looking for a romantic night out, you can enjoy seasonal American cuisine from Executive Chef Andrew Zimmerman at Sepia.

Rtip: Besides deep dish pizza you’ll want to find yourself a Chicago-style hotdog. Portillos is a mainstay but anywhere you see the Vienna Beef neon sign you’re good to go, just don’t ask for ketchup. Need more ideas? Our contributors’ favorites have been outlined in our day-to-day itinerary.

Where can we get a good cocktail?

Here’s a secret. If you want great city night views, head to 875 N. Michigan Ave. (formerly known as the John Hancock Center) and go to the Signature Lounge at the 96th floor. The drinks are a little more expensive, but the view is worth it. There are also some really cool Blues Bars worth checking out, including Buddy Guy’s Legends and Blue Chicago. 

Where should we shop?

If you are looking for high-end retail, Michigan Avenue is the place to shop in Chicago, including Water Tower Place near Macy’s. However, many of Chicago’s neighborhoods like Wicker Park & Bucktown are home to cute specialty shops. You'll have to grab an Uber to get out there but there are a few gems that pepper the area.  It's much more "hipster" and you have to do a little hunting for the best shops but places like T-Shirt Deli are worth the haunt. You’ll also find quaint boutiques including Alice & Wonder in Lincoln Park, which curates super cute Chicago tees. 

What should we take with us?

I always travel with a scarf as it is so versatile. They are light and easy to carry in your daypack and if the temperature unexpectedly drops or a museum is too cool, it will keep you warm. It can also dress up any outfit, even a t-shirt and jeans.

Rtip: There is a reason it’s called the “Windy City” and that’s the lake effect, which also impacts the windchill and snowfall, humidity levels and impossible heat. Go with layers and stay comfortable, whatever the season.

Tell us something you don’t know?

The Chicago River is the only river in the world to flow backward. Civil engineering reversed the river's natural direction towards Lake Michigan to the Mississippi River Basin.

What would you do differently on your next trip?

Skip the Field Museum. You only want to spend so much of your time inside museums and this is the one I’d bypass, unless you are a huge history fan.