How to Plan a Weekend Getaway to Chicago

How To Plan Your Weekend Getaway To Chicago
You’ve got a weekend free and decided to take a trip to Chicago. The bustling and beautiful city offers plenty to do, so you want to make the most of it. The largest city in Illinois, Chicago has over 77 unique community areas, each with its own distinctive neighborhoods and personalities that offer opportunities for sightseeing, dining and entertainment. People come from all corners of the world come to experience all that Chicago has to offer. In fact, Chicago hosted a record-breaking 54 million domestic and international travelers last year alone.

Chicago Hosted A Record-Breaking 54 Million Domestic and International Travelers last year alone.

Whatever you’re planning — a girl’s or guy’s weekend, a romantic getaway for two or just a short trip alone to explore the sites — your perfect Chicago visit awaits. The Choose Chicago website is a great place to start your planning. It offers a suggested list of themed itineraries for everyone from the food lover to the history buff. It also contains other helpful visitor resources such as current weather, driving distances, city maps and attraction discounts.

Chicago is home to over 7,300 restaurants, nearly 200 theatres and art galleries and 552 parks. Factor in the beaches, museums, and cultural and historical sites and you’ll see that there’s no shortage of things to do. Grab your comfy shoes, leave plenty of room for food and drink and plan on pushing back your bedtime considerably.

Chicago is home to over 7,300 restaurants, nearly 200 theaters and art galleries and 552 parks.

Where to Stay

The city of Chicago is divided into 9 different districts, also called “sides,” which include:

  • Central
  • Far North Side
  • Far Southeast Side
  • Far Southwest Side
  • North Side
  • Northwest Side
  • South Side
  • Southwest Side
  • West Side

The districts can be consolidated into the regions of North, West, Downtown and South, each of which is home to smaller community areas that combine to feature over 100 distinct neighborhoods. Here are some of the many popular tourist areas in Chicago:

  • The Loop. Also known as Downtown, this area is home to many beautiful parks, buildings and cultural happenings. Downtown Chicago is about a 45-minute ride from O’Hare airport. Staying downtown will put you in the middle of everything, but will cost more than staying in other areas.

    Staying Downtown Will Put You In The Middle Of Everything, But Will Cost More Than Staying In Other Areas.

  • Lincoln Park. This beautiful neighborhood located just north of downtown offers beautiful scenery, eclectic shops and ethnic restaurants. Its namesake park is a beautiful, 1,200-acre space that is home to the Lincoln Park Zoo, which features free admission. Lincoln Park is also home to many museums, theatres and live music and entertainment venues.


  • Magnificent Mile. This eight-block neighborhood features over 450 stores, luxury boutiques and shopping malls along with many restaurants and hotels. Big names include Macy’s, Nordstrom and Saks Fifth Avenue to name a few. For high-end shopping and dining, this is the place to be. The Magnificent Mile also features many beautiful historic, architectural and cultural sights for those who wish to enjoy the area without the shopping experience.

  • Bucktown/Wicker Park. This pair of adjacent neighborhoods — which are usually referred to as being one and the same — is located just outside the downtown area. It has a great nightlife scene with live music, trendy bars and eclectic shops. This area is also home to many upscale and highly sought after Michelin-rated restaurants.

  • River North. This evolving urban neighborhood is located adjacent to the Loop and Magnificent Mile. It is a haven for fine art and design with its art galleries, antique stores and unique buildings. Cuisine from all around the world is represented at the many restaurants in River North. The neighborhood also offers a lively nightlife scene with a host of bars, lounges and nightclubs.


Getting the most out of your brief time in Chicago need not take a huge amount of planning. Make sure to make hotel and dining reservations at popular eateries prior to your visit. Figuring out where to stay in Chicago is simply a matter of preference.

The city of Chicago boasts over 40,000 hotel rooms in its central business district alone. Luckily, with the large selection of travel planning websites such as Orbitz, Travelocity and Trivago, it’s quite easy to score a great rate on last-minute hotel rooms for a few nights. Travel sites will even assist you in obtaining a rental car if needed.

The city of Chicago boasts over 40,000 hotel rooms in its central business district.

If you’d rather walk your way through the city, which is a very popular choice for many visitors who wish to take their time while seeing the sights, there’s plenty of attractions within walking distance of each other. Be sure to use the helpful interactive city map located on the Choose Chicago website. It gives you realtime directions and lists nearby attractions.

You can always take a taxi or grab a ride from Uber or Lyft. Public transportation is available through the Chicago Transit Authority’s L train — you’ll need a CTA Visitor Pass to ride — and buses with routes traveling all through the city. If traveling to or from the Chicago suburbs, the Metra train provides an affordable transportation option with unlimited weekend rides for $7.

Bicycles are available to rent for those who wish to cycle their way through the city. Bicycle rental shops will also provide you with a lock for parking and locking your bicycle.

Chicago Nightlife

Chicago can be considered a city that never sleeps, as the abundant nightlife scene keeps the city buzzing long after the sun goes down. You can find fun things to do after dark in just about every Chicago neighborhood. Consider the following options:

  • Comedy Clubs. Comedy is very popular in Chicago. In fact, many famous comedians such as John Belushi, Tina Fey and Steve Carell got their start in the Windy City. Legendary comedy clubs such as The Second City and Zanies, both of which are located in Old Town, feature a wide variety of comic acts sure to keep you laughing.

  • Music Clubs. Chicago is home to over 225 live-music venues that span every genre from classical to rock. These clubs range from small intimate stages to large multilevel venues with stadium seating. The Green Mill Jazz Club offers live jazz music every night with its elegant speakeasy atmosphere as the backdrop. Reggies Chicago is a rock club featuring live music from many different genres, a record store and a roof deck. The Vic Theatre, a former vaudeville house that now features live rock and pop bands, also doubles as a movie theatre. The historic Chicago Theatre is a large auditorium that seats 3,600 people and hosts music acts from all different genres.

  • Bars and Nightclubs. The city’s many bars and nightclubs keep the city hopping throughout the night. With so many different bars, taverns, lounges and nightclubs in the Chicago area, making a list of them is almost impossible. Fortunately, the Chicago Metromix website offers an easy way to choose where you want to go. This site allows you to filter bars by neighborhood, bar style, extra features such as live music or outdoor seating, and meals served.

  • Nighttime Helicopter Tours. If the bar scene isn’t your thing, there’s still plenty to do at night. Consider taking a nighttime helicopter tour over the Chicago skyline. Fly over the beautiful sights in a heated helicopter while your pilot serves as your tour guide. This 15-minute tour takes you over such sites as Navy Pier, Wrigley Field and Millennium Park.


Fly over the beautiful sights in a heated helicopter while your pilot serves as your tour guide.

Chicago Through the Year

No matter when you come to Chicago, you’ll never lack for things to do. Chicago boasts an impressive calendar of annual events that keep the city hopping. Here are some of the many seasonal activities offered each year:

  • Winter. Bundle up and visit one of the many outdoor ice-skating rinks, such as at Millennium Park and Wentworth Park. There are also a variety of indoor rinks as well, such as the one at Navy Pier during its annual Winter WonderFest. During the holidays, attend the Christkindlmarket, an outdoor German Christmas market featuring homemade goods and delicious food such as sausages, potato pancakes, sauerkraut, sweets, beer and spiced wine. Catch a Chicago Bulls basketball game at United Center during their season that runs from October through April.
  • In the winter, bundle up and visit one of the many outdoor ice-skating rinks, such as at Millennium Park and Wentworth Park.

  • Spring. Visit one of the many farmer’s markets and festivals, featuring food vendors and local goods. See some of the beautiful spring blooms at one of Chicago’s parks and conservatories such as Lincoln Park Conservatory and Garfield Park Conservatory. Arboretums and botanical gardens also provide a beautiful backdrop for picnicking and strolling or hiking. Celebrate St. Patrick’s Day at one of the many Irish pubs around the city or watch one of the two parades held that day. Kick off the day by watching the annual dyeing of the Chicago River, which turns the river from its usual dark green to a bright shade of emerald.
  • Summer. Take advantage of the warm weather and swim or sunbathe along the beautiful shores of Lake Michigan. Many of these beaches feature snack bars, restrooms, and bicycle and jet ski rentals. Have a picnic and enjoy the warm summer air while attending one of the free summer concerts held in Millennium Park. Visit one of the many food and music festivals held in Grant Park or check out the annual Taste of Chicago festival, which is usually held around Independence Day each year.
  • Take advantage of the warm weather and swim or sunbathe along the beautiful shores of Lake Michigan.

  • Fall. Watch a Chicago Bears football game at Soldier Field or if you don’t feel like braving the chilly fall air, visit one of the many local taverns, such as McGee’s, that offer great food, snacks and drinks to help you cheer on the local team. View the beautiful fall foliage while enjoying the various wine, cheese and spirits tasting events throughout the city. Attend one of the many fall festivals that take place in and around the city, such as artwork exhibit EXPO CHICAGO at Navy Pier and the Bacon and Beer Classic at Soldier Field.

Places to See and Things to Do

If you’re looking for something fun and memorable, check out the following attractions:

  • Wrigley Field. If you’re in town during baseball season, catch a Cubs game at the historic Wrigley Field. If you can’t snag tickets, watch the game through the keyhole, a small opening on Sheffield Avenue through which you can see into the stadium. Wrigley Field also offers daily tours from April through October.
  • If you're in town during baseball season, catch a Cubs Game at the Historic Wrigley Field.


  • Grant Park. This 319-acre space is affectionately known as Chicago’s front yard and is named for former President Ulysses S. Grant. Grant Park is the location for many annual concerts, festivals and other public gatherings. One of the main features of the park is the beautiful Buckingham Fountain, which puts on light and water displays from April through October.

  • The Art Institute of Chicago. This world-famous art museum and school contains many famous works of art by artists such as Picasso and Seurat. Daily tours are offered and special exhibitions are featured throughout the year.

  • Millennium Park. This beautiful park features artistic works and beautiful gardens. Visit the iconic Cloud Gate sculpture, otherwise known as “The Bean,” for its bean-like shape. No visit to the city would be complete without a picture in front of this shiny metallic masterpiece.

  • Navy Pier. While Navy Pier offers a 150-foot high Ferris wheel, there are plenty of adult things to do as well. Overlooking Lake Michigan, Navy Pier offers a variety of activities including boat tours, an IMAX theatre and live seasonal entertainment. Visit the Landshark Beer Garden or Margaritaville to enjoy scenic views of the Chicago skyline while enjoying a refreshing beverage or two.

  • 360 Chicago Observation Deck. This awesome Chicago site, formerly known as the John Hancock Observatory, offers a new attraction called Tilt that is certainly not for the faint of heart. Visitors can experience views from 1,030 feet above while looking straight down from a clear glass enclosure that extends out over the city.

  • Willis Tower Skydeck. Formerly known as the Sears Tower, this iconic building frames Chicago’s skyline. Travel to the 103rd story and view all of Chicago and Illinois, as well as Indiana, Michigan and Wisconsin.

  • Lake Michigan Trail. This beautiful lakefront trail is 20-miles long. It is good for walking, running or bicycling and will take you around many great Chicago sights. On warm days, you can take a dip in the lake or enjoy the beach.

Where to Eat

When visiting Chicago, you’ll find no shortage of dining options. From casual to themed to upscale, there are places to eat at every turn. Choosing where to eat is guaranteed to be the most difficult part of your stay.

More than a cup of coffee and a place to sit down and check your email, Chicago’s numerous coffee shops offer visitors much versatility in planning meals. Conveniently located all around the city, including inside many hotels, coffee shops offer meal options from breakfast to lunch and sometimes dinner.

Consider grabbing breakfast or a light snack at a Chicago coffee shop. Here you can sample some of the many varieties of coffee, tea and hot chocolate from both local and international sources. Chicago’s coffee shops are perfect for getting warm on a cold winter day or for cooling off with an iced beverage during a warm summer afternoon.

You can make an adventure of your coffee shop visit. Visit some iconic movie history in Chicago’s Wormhole Coffeehouse in Wicker Park, which houses Marty McFly’s infamous DeLorean from the Back to the Future films. Some coffee shops, such as Metric Coffee in Fulton Market, offer workshops on brewing coffee at home.

No visit to Chicago would be complete without sampling some of its renowned deep-dish style pizza. Be sure to visit us in one of our locations in and around the city for a taste of our 200-year-old stuffed pizza recipe deemed “Chicago’s best” by millions! You can relax with a drink over lunch or dinner, or take a piping hot pizza back to your hotel. Giordano’s also offers a variety of appetizers, sandwiches and salads along with its many varieties of award-winning pizza.

For a quick but satisfying bite, grab a Chicago-style hot dog at Wrigley Field’s Wrigleyville Dogs or Wolfy’s. These world-famous hot dogs feature all-beef dogs on a poppy seed bun. The variety of toppings is endless and varies according to location but usually includes mustard, relish, chopped onions, sliced tomatoes, peppers, pickles and celery salt.

Though not all restaurants in Chicago require a reservation, it’s always a good idea to call as soon as you know where you wish to dine. Fortunately, making dining reservations has never been easier thanks to some popular apps such as Open Table, which allows you to explore restaurant menus and make reservations. It’ll even send you a reminder. Table Savvy is great for last-minute dining reservations. The app searches last-minute reservations and provides a substantial discount off your dining bill for a $5 reservation fee.

Here's a few tips that will help you have a great time without breaking your wallet:

Planning on a Budget

For those who wish to experience Chicago while staying on a budget, here’s a few tips that will help you have a great time without breaking your wallet:

  • Consider staying in a hotel outside the city. These hotels usually offer fares that are quite a bit lower than those located in the city. Public transportation via the Metra train offers an affordable opportunity to see more of the beautiful city.
  • Split a cost of a hotel. If planning a girl’s or guy’s weekend, where staying in the heart of the city is a must, consider splitting the cost of a downtown hotel to be close to nightlife, restaurants, shopping, sports and spas.
  • Grab a snack at one of the many farmer’s markets and festivals. These markets usually feature a wide variety of food vendors offering fruits, vegetables and other tasty gourmet eats that will cost you less than a restaurant meal.
  • Take advantage of some of the free or self-guided tours. Offered at many places in Chicago, such as the Chicago Cultural center, you can explore the area through free events such as concerts, exhibits, film screening and lectures.
  • Bring your own bottle (BYOB) to restaurants. These restaurants are usually much more affordable than those that serve alcohol. The cost of buying your own beverage is also much less, and many restaurants will not charge you a corkage fee for opening your bottle.

Nearby Places

If you have a little time left over or want to take a day to see what lies just outside the city, consider one of these places that can be reached within about an hour or two from Chicago:

  • Evanston, Illinois. Located just 15 miles north of Chicago and a short train ride away, this beach town offers quaint bed and breakfasts, a lighthouse and other relaxing activities including distillery and campus tours.
  • Crystal Lake, Illinois. This beautiful town located 50 miles northwest of Chicago features a beautiful recreation area on the lake, complete with beach, hiking trails and boardwalk. The downtown area offers shopping and dining. While public transportation from the city is available, driving is recommended if you want to see both areas.
  • Starved Rock State Park. For the adventurous traveler, this scenic state park is located 100 miles southwest of Chicago. Nestled along the Chicago River, it features canyons, waterfalls and hiking trails. There are also guided hiking and paddleboat tours available.
  • Bloomington-Normal, Illinois. This town, 130 miles southwest of Chicago, features restored buildings that house shops, live music venues and restaurants featuring local fare. During the summer months, you can experience the works of Shakespeare during the annual Illinois Shakespeare Festival.

After a fun and action-packed weekend in Chicago, you’ll probably be a little tired but ready to plan your next trip. If you’re already missing that mouth-watering taste of Chicago-style deep-dish pizza, you can have it shipped directly to your door. Visit the Giordano’s website for complete information about how to get your next deep-dish pizza fix — it’s just what you need to tide you over until your next visit.