4 days in Chicago - the perfect itinerary for first-time visitors

This guide presents the perfect itinerary for first-time visitors to Chicago with an itinerary for 4 days of sightseeing, eating & having fun!

Chicago is the birthplace of the skyscraper, and if you're an architecture fan, it's a "must visit" city. I lived in Chicago for 15 years, and although I haven't lived there for a while, I love to visit on a regular basis. There are so many things to love about Chicago - the architecture is beautiful; it's steps away from the shores of Lake Michigan; it's home to some amazing museums and is a big sports town.

This itinerary is written for a first time visitor to the city, who would like to experience the highlights of the city over a 4 day long-weekend.

Jump to:

• Planning a visit to Chicago
• Where to Stay in Chicago
• Four Days in Chicago - The Perfect Itinerary
• Must eat!
• Final Thoughts
• Chicago Hotel Reviews

Planning a visit to Chicago

The first question most people will have is "When is a good time to visit Chicago"? Unless you're a fan of frigid weather, you'll want to stay away from Chicago in winter - it's beautiful when the city is covered in a fresh layer of snow, but otherwise, the should be avoided from late December through until early March. It's been said that the reason that Chicago has such awful winters is because if she didn't, everyone would want to live there.

I think that the best times to visit Chicago are in May, when the weather is starting to warm up, or in late September through early November, when it's not so humid, and the museums are less crowded.

Chicago has two major airports - O'Hare International, and Midway; both airports are serviced by Chicago's famous L (Elevated Trains); O'Hare is at the junction of the Blue Line, and Midway is at the junction of the Orange Line. You can board a train by swiping a credit/debit card at the turnstiles, or you can single or multi-day tickets from a vending machine at the station. O'Hare is less than 40 minutes by train from the Loop, and Midway is 25 minutes away; both train lines are very convenient, and generally can get you into town in about the same amount of time as a cab or Uber.

Where to Stay in Chicago

Budget Accommodation: Holiday Inn Express Magnificent Mile

This hotel is a couple of blocks in from N. Michigan Avenue; it's close to Michigan Avenue Shopping, and a plethora of restaurants. The hotel was build in the 1920s as The Hotel Cass; it has a charming lobby; however, the rooms are tiny, so I would only recommend this hotel for solo travelers.

Midprice:

I have a few mid-price recommendations; look for reviews of each of these hotels here on the blog in the next week or so. Depending on the time of year, and what's happening on any given weekend, these hotels can be booked for as little as $125 a night.

• InterContinental Chicago Magnificent Mile

Located on N. Michigan Avenue, just a couple of blocks north of the Chicago River, this hotel is central to everything. If you're looking to go to Navy Pier, the entrance to the walkway to Navy Pier is right outside the hotel. Michael Jordan's Steakhouse is located inside the hotel, and one of the most unexpected features of the hotel is the amazing indoor swimming pool on the 12th floor of the hotel.

• Hyatt Centric The Loop Chicago

Chicago's Business District is located in "The Loop" (named after the elevated train tracks that loop through the city). This hotel's location is close to Willis Tower (as a long-time Chicago resident, I still fondly call it The Sears Tower). It's also just a few short blocks from Millennium Park on S. Michigan Avenue; it's convenient to multiple train lines.

• Hyatt Place, Chicago/River North

This hotel is located on N. Wabash Ave, just a few blocks off N. Michigan Avenue. It's convenient to lots of restaurants, including Portillo's, for hot dogs or Italian Beefs! The rooms include a bedroom and sitting area with a "cozy corner" - a sectional couch, which is great if you're looking to just relax after a day of sightseeing.

• Hyatt Regency, Chicago

Chicago's largest hotel is the Hyatt Regency Chicago, with 35 floors, 2,032 rooms, and 123 suites located on E. Wacker Drive, right across the street from the Chicago River, and next door to the Chicago Architectural Center. It's just a few blocks north of Millennium Park.

Luxury: Park Hyatt, Chicago

Park Hyatt Chicago is a 5-star hotel located on N. Michigan Avenue, close to the historic Water Tower Park and famed Michigan Avenue and Oak Street shopping. The hotel exudes elegance with amazing views over Lake Michigan. Make sure you pet Parker, the hotel's resident pug, who reigns over the lobby.

Four Days in Chicago - The Perfect Itinerary

My itinerary is flexible, so don't feel like you have to do each day in order; if you're planning on seeing a sporting event, you'll be subject to game days!

Day One

Chicago is famed for its architecture, so taking an Architecture tour is a must! Tours are available in a number of formats, but my favorites are either a walking tour, or a Chicago Architecture River Cruise.

Visit Chicago Architecture Center to get some ideas. The Chicago Architecture Center is a non-profit organization; their shopfront is at 111 E. Wacker Drive, conveniently located across the street from the Chicago River, and almost of the corner of Michigan Avenue, one of the main shopping streets in Chicago. From there, you can visit one of their exhibits, or buy tickets for one of the many tours offered.

While you're exploring Chicago's skyscrapers, I recommend a visit to either the top of Willis Tower or 875 N. Michigan, formerly known as the John Hancock Center, for awe-inspiring views; on a clear day, you can see four states - Illiniois, Indiana, Michigan, and Wisconsin from the 94th floor. If you're not scared of heights, visit The Ledge, a glass-enclosed balcony at Willis Tower. Definitely not something for the faint of heart!

Day Two

Explore a couple of outdoor attractions.

I recommend starting at Millennium Park (which is practically next door to the Art Institute on S. Michigan Avenue.). The park is bounded by Michigan Avenue, Randolph Street, Columbus Drive and East Monroe. In 2017, Millennium Park was the top tourist destination in Chicago and in the Midwest, with over States with 25 million annual visitors.

The park is famous for its outdoor art pieces - Cloudgate (affectionately called "The Bean" because of its shape), The Pritzker Pavilion (a bandshell designed by Frank Gehry), The Crown Fountain (an interactive display, much beloved by small children in summer, who play in the "dancing water".) Frank Gehry also designed the BP Bridge.

In summer, the park hosts outdoor concerts at the Pritzker Pavilion, and in winter, there is an outdoor ice skating rink.

Navy Pier on the Lake Michigan lakeshore is home to Centennial Wheel, a large ferris wheel which offers great views of the Chicago skyline. Did you know that the first Ferris Wheel was constructed as a landmark for the 1893 World's Columbian Exposition in Chicago?

Personally, I would rather spend an afternoon at Millennium Park than Navy Pier - I associate Navy Pier with overpriced souvenirs and bad food choices...

Day Three

Visit a Museum (or two!) - Chicago has a number famed museums, including:

The Art Institute: The Chicago Art Institute is located on S. Michigan Avenue, and can't be missed - look for the two bronze lions flanking the entrance. The museum has almost 300,000 pieces of art in its permanent collection, including American Gothic, arguably the most famous American painting of all time.

Field Museum: The Field Museum is a natural history museum, located in the "Museum Campus" area south of the Loop (in this area you'll also find the Shedd Aquarium, the Adler Planetarium, and Soldier Field, home of the Chicago Bears).

The company I work for celebrated their 50th anniversary last year with a gala evening event at the Museum - it was fun to explore the museum after-hours. It had a "Night At The Museum" vibe (without the exhibits coming to life!). If you have a child who is a dinosaur fan (and aren't they all?), there is an amazing collection of dinosaurs and bones at this museum, sure to delight children of all ages.

Museum of Science & Industry: This museum is located in the Hyde Park neighborhood on the southside, close to the campus of the University of Chicago (and former President Obama's Chicago residence). It's loved by children & adults alike. The Museum of Science & Industry boasts an IMAX theater inside, and a WWII era U-Boat outside.

Day Four

Take in a sporting or cultural event.

For Sporting fans, depending on your interests, Chicago is home to a number of professional sports teams including two baseball teams, the Chicago Bears who play at Soldier Field, and the Chicago Bulls (basketball) and the Chicago Blackhawks (Ice Hockey) who both play at the United Center just west of the loop.

If visiting during summer, seeing a baseball game is a must-do for any baseball fan. Visit the Chicago Cubs at Wrigley Field in Lincoln Park, and the Chicago White Sox at Guaranteed Rate Field, formerly Comiskey Park and U.S. Cellular Field, on the southside (off 35th Street). Both baseball fields are accessible by The Red Line, one of the routes of the L train. In my opinion, there is nothing more "Chicago" than spending an afternoon at Wrigley Field in the middle of summer.

For those who prefer the Arts, Chicago is home to the Chicago Symphony Orchestra, (who have won more Grammys than any other Orchestra). They perform at the Symphony Center on S. Michigan Avenue, practically across the street from the Chicago Art Institute. Chicago is also home to the Civic Opera House, the Joffrey Ballet, and for those who like comedy, the original Second City (stomping grounds of many SNL alumni...)

Must eat!

Chicago is a foodie lover's delight, from street food through to world-famous Michelin-rated restaurants. My recommendations for places to eat are more on the "casual" size, and IMO, should be tried by anyone visiting Chicago for the first time. These are my favorite places to visit, and I look forward to Chicago visits if for nothing else than to get my "fix" of some of these foods.

Deep Dish Pizza: Everyone has their favorite, from Lou Malnati's, to Pizzeria Uno, Pizzeria Duo, and Giordano's. Mine is Giordano's, with locations in The Loop, the South Loop, West Loop/Greektown, and Gold Coast/Magnificent Mile.

Chicago Hot Dog: Nobody in Chicago over the age of 12 would be caught dead putting ketchup on their Hot Dog. A Chicago Hot Dog starts with a lightly steamed poppy-seed bun, an all-beef hot dog loaded with mustard, relish, celery salt, freshly chopped onions, sliced red ripe tomatoes, kosher pickle and sport peppers. My favorite Hot Dog place is Portillo's, on N. Clark in River North.

Lou Mitchell's: This diner is located on W. Jackson Street, just a couple of blocks west of Willis Tower. Lou Mitchells has been serving locals and tourists since... It's the place where television news shows will go when they want an opinion from the "average man on the street" - during election season, you'll see presidential candidates stopping in for breakfast and to "press the flesh". Carter, Reagan, Clinton, Obama, and both Bushes have eaten at Lou Mitchell's (I'm pretty sure Trump hasn't eaten, but haven't found evidence of a visit by Joe Biden...)

Lou Mitchell's is strictly a breakfast and lunch place, so get there early. I will eat breakfast anytime of the day - I love their Banana Pancakes, Sour Cream Omelet (imagine if a baked potato was an omelet!), and even eggs with sausage and their skillet potatoes.

Final Thoughts

Chicago is one of my favorite cities to visit; hopefully, a four day visit will whet your appetite for a return visit to explore the city further.

If you've been to Chicago, or live in Chicago, what is your favorite part of Chicago? Leave me your thoughts in the comments!

Chicago Hotel Reviews