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This is the Social Tourist’s ultimate travel guide to the perfect things to do in Chicago, Illinois this weekend. There are so many sites to see in Chicago; a weekend stay is not enough to see it all. I’ve lived in the City of Chicago for 30 years and it still never gets boring to me. Chicago is always evolving so it’s impossible to get bored.
Chicago’s nickname, Windy City, dates back to the late 1870s. Then editor Charles A. Dan of the newspaper the “New York Sun”, wrote that “Chicago was windy because of its politicians being full of hot air.” The city is still very political. But we also know how to have fun.
A visit to the city of Chicago is a visit to a city known for its beautiful skyline that frames Lake Michigan, its sports teams and its relationship to hot dogs and pizza.
The weather in Chicago is such a major player that it deserves its own heading. It plays a big role in how Chicagoans and visitors interact with the city.
The best times to visit Chicago and not encounter snow and extreme cold is between late April/May and mid-October. I’ve always said that there’s only two seasons in Chicago; Summer and Winter.
And with those 2 seasons come the extremes in temperatures. Seriously though Chicago does have 4 seasons. Spring and Fall are very short and dominate less than Summer and Winter.
However, Chicago prides itself on continuing life and fun even during the worst Chicago’s weather has to offer. Even during one of the coldest months, there are things to do in Chicago in December.
Directions to Chicago
Chicago is located in the upper portion of Illinois. Using your left hand as a navigational reference guide the city of Chicago would be located along the curvy part of the web between your index finger and thumb….well, sort of.
Airports in Chicago
There are 2 airports that serve the Chicagoland area; Chicago O’hare Airport (ORD) and Chicago Midway Airport (MDW). You are going to have plenty of ground transportation options once you land. However, the fastest and cheapest way to get downtown is by public transportation. Both airports are easily accessible by public transportation; the Chicago ‘L’ trains.
Traffic from the airports is horrible unless you fly in very early or late (after 7 PM). Unless you love sitting in mind-numbing traffic, I recommend taking the ‘L’. During rush hour (6 AM- 10 AM and 2 PM – 6:30-7PM), it can take up to 2 hours to reach downtown from either airport (even though MDW is a lot closer to downtown).
The train from ORD to downtown Chicago takes 40-45 minutes (Blue Line). The train from Midway to downtown Chicago takes about 20-minutes (Orange Line). You can click here for more information on public transportation in Chicago.
Please note: Keep in mind that Chicago is serviced by 2 airports, ORD and MDW when making your plane reservations.
Looking to do a Chicago Getaway? Click here to compare airline prices to Chicago.
Read more on buying airfare by reading “Best Time to Buy Airline Ticket“
Staying Safe in the Big City
Yes, parts of Chicago can be dangerous. But don’t most cities (both U.S. and abroad) have parts that are considered not safe. But with a little street-savvy and awareness of how you’re presenting yourself, you will be fine.
- Just like any city that you visit, always be aware of your environment.
- Try not to appear touristy.
- If you’re like me and love carrying huge-ass purses, make sure the purse has a shoulder strap that you can wear across your body.
- Never leave your purse on the back of your chair. Especially if you are enjoying a meal at one of Chicago’s many sidewalk cafes/restaurants.
- Do not take shortcuts through alleys. No matter how tempting.
- When going out at night, stick to well-lit sidewalks, main streets, and parks. The lakefront is gorgeous at night. Full of good people with neighborly and friendly mid-western values. Join them and enjoy the amazingly beautiful city that is Chicago. I never get tired of the welcoming energy of my city.
- Enjoy yourself.
The downtown area and all neighborhoods are heavily patrolled by the City of Chicago Police. Some neighborhoods such as Hyde Park and parts of Lincoln Park are also patrolled by University Police. So like I said…feel free to enjoy yourself but do it safely.
Where to Stay in Chicago
I recommend staying in or around downtown Chicago. It’s not cheap but it’s also not impossible to find awesome deals on Chicago hotels. Click on Booking.com for the latest rates on the best hotels in Chicago. It’s all about timing. Obviously, the best time to catch a deal on hotel rates in Chicago is during the winter time. Late November, early December and the month of February are when you will find the cheapest rates.
Chicago is a city that is extremely passionate about sports. No matter what time of year you choose to visit Chicago you can find a sporting event of some type.
- Chicago Bears – You can see the Bears play football at Soldier’s Field (1410 Museum Campus Dr. – Downtown Chicago Loop) For more information on the Chicago Bears, go to ChicagoBears.com.
- Chicago Cubs – The Chicago Cubs play at Wrigley Field (1060 W. Addison St. – Chicago neighborhood of Wrigleyville), one of the last remaining old-school baseball fields left in the United States. For more information, click here.
- Chicago White Sox
- Chicago Bulls
- Chicago Hawks
Downtown Chicago – My kind of town
My heart still skips a beat of excitement every time I go downtown; even after 30 years! It’s a great jumping off point for Chicago attractions and fun things to do in downtown Chicago. Its centralized location also makes it perfect for exploring the many neighborhoods that make up the city of Chicago. And there are plenty of day trips possible to the suburbs, Indiana, Michigan and Wisconsin.
The downtown area of Chicago is made up 6 different neighborhoods. Each neighboorhood has its own character and charm.
- The Loop
- River North
- Magnificent Mile
- Gold Coast
Map of Downtown Chicago
Later on in this post, I will be breaking down each downtown neighborhood and exploring the following:
- Chicago Museums
- Best hotels in Chicago downtown
- Fun things to do in downtown Chicago
- Shopping downtown Chicago
- Downtown Chicago attractions
- Downtown Chicago events
- Best things to do in Chicago when you only have a few days
- Things to see in Chicago outside of downtown
- Chicago restaurants
Public Transportation – Chicago has one of the best public transportation in the world. Buses run every 10-15 minutes depending on the route. Trains run every 7-10 minutes during the day and every 10-15 minute after evening rush hour. For more information, go to www.transitchicago.com.
Recommendation: Google Maps is very useful in navigating Chicago public transportation.
Other means of getting around Chicago includes Uber, Lyft or Taxi.
Parking downtown Chicago – Parking in downtown Chicago is expensive. Street parking downtown is metered and costs about $6.50 per hour. Meters accept credit cards or you can use a parking app. I recommend reading “Parking in Chicago” by Local Tourist for a great breakdown on parking in the downtown area.
The Chicago Loop – The Neighborhood that Works
What is the Loop in Chicago? I consider the Loop area of downtown the heart of Chicago. The Loop got its name from the fact that the elevated trains “loop” around this area of downtown.
The Loop area of downtown Chicago includes the business and theater district. The action settles down after business hours when everyone heads home. During the day, is the best time to see the Loop in action.
Map Chicago Loop
Best Places to Stay in Chicago Downtown Loop
If you really want to get to know this fine city, up-close and personal, downtown is the place to stay.
What are the best hotels in downtown Chicago? I mean any hotel downtown will just about do. You will be within walking distance of shopping, tours, attractions, and the lakefront.
I will break down where to stay in Chicago Loop downtown by area. Here are just a few recommendations from a long list of recommendations; check prices from Booking.com:
Loop Hotels on Michigan Ave
- Best Western Grant Park – 1100 S. Michigan Avenue
- Hilton Chicago – 720 S. Michigan Avenue
- Blackstone Hotel Chicago – 636 S. Michigan Avenue
- Congress Plaza Hotel – 520 S. Michigan Avenue
Loop Hotels off Michigan Ave
- Travelodge by Wyndham Downtown Chicago – 65 E. Harrison St
- Hotel Blake – 500 S. Dearborn St
- Central Loop Hotel Chicago – 111 W. Adams St
- JW Marriott Chicago – 151 W. Adams St
- W Chicago City Center – 172 W. Adams St
- Palmer House – 17 E. Monroe St
Click here to check hotel prices through Booking.com
Chicago Loop Attractions, Museums, and Landmarks
Chicago Lakefront Trail
The Chicago Lakefront Trail is an 18-mile for running, walking and biking. A portion of the trail runs along the lakefront from Roosevelt Road to the Chicago River in the Chicago Downtown Loop. The views of Lake Michigan and the skyline are breath-taking. Not to be missed!
Recommendation: Make sure to cross Lake Shore Drive at designated over/underpasses or crosswalks to get to the Lakefront Trail. Click here for a map of the trail.
Soldier’s Field (1410 Museum Campus)
Opened in 1924 and the home of the Chicago Bears since 1971. Soldier’s Field sits on 17-acres of parkland. The field is open to the public year-round and the surrounding parklands include a children’s garden and Veteran’s Memorial. Admission: Free
Grant Park (337 E. Randolph St)
Grant Park stretches 5 blocks from Roosevelt Road to Randolph Street. A number of events are held at this park such as Lollapalooza, Taste of Chicago and much more. For more information on events go to grantpark.org. You can find the following attractions and landmarks at Grant Park
- Buckingham Fountain (301 S Columbus Dr) – Located in the center of Grant Park (337 E. Randolph St), it is one of the largest fountains in the world. Runs from 8 AM – 11 PM daily, from early May through mid-October. Admission: Free
- Millenium Park (201 E. Randolph) – it part of Grant Park and includes the Cloud Gate, Crown Fountain, Lurie Garden, and Jay Pritzker Pavillion – just to name a few. Admission: Free for a lot of the events. For more information on events, prices, parking, etc at Millenium Park, click here.
Field Museum Chicago(1400 S Lake Shore Drive)
- Founded in 1893 as part of the World’s Columbian Exposition, the Field Museum is home to world-class scientific researchers, extraordinary exhibits and Sue, the T-Rex.
- Admissions: Adult – $24.00 Child – $17.00
Recommendation: If you’re not all museum-ed out by now, check out the entire Museum Campus (1400-1562 S. Lake Shore Drive).
- Shedd Aquarium (Admissions: Adult – $39.95 Child – $29.95)
- Adler Planetarium. Admissions: Adult – $24.95 Child – $19.95
To gain entry and to save money use your Go Chicago Card.
Art Institute of Chicago (111 S Michigan Ave)
- The Art Institute of Chicago was founded as both a museum and a school of fine arts in 1871. However, the Art Institute didn’t find it’s present home until 1893 when the building, flanked by 2 lions, was built for the World’s Columbian Exposition. The Art Institute of Chicago houses a permanent collection of more than 300,000 paintings, exhibits, and artifacts. There is something for the art lover in all of us at this museum. Expect to spend at least a couple hours in this large museum.
The Art Institute of Chicago houses a permanent collection of more than 300,000 paintings, exhibits, and artifacts. There is something for the art lover in all of us at this museum. Expect to spend at least a couple hours in this large museum.
- Admissions for Art Institute of Chicago – Adult – $25.00 Child under age 14 – Free. Special Exhibits could cost extra. For information, go to artic.edu.
Chicago Symphony Center (220 S. Michigan Ave)
For more information on tickets and events, go to cso.org.
Chicago Theater District
- Chicago Theater – (175 N State St)
- Oriental Theater – (24 W. Randolph St)
- Cadillac Palace – (151 W. Randolph St)
- Goodman Theater – (170 N. Dearborn St)
For more information about shows, go to broadwayinchicago.com.
Chicago Board of Trade Building (141 W. Jackson Blvd)
- One of Chicago’s famous architectural landmarks. the Chicago Board of Trade Building’s Art Deco facade has been featured in a number of movies such as “Batman Begins” and “Man of Steel”.
- Can be seen as part of a number of walking tours. If you’re into architecture and want to learn about how it shaped Chicago and its history it can be seen as part of a number of walking tours.
- Recommendation: Check out the Chicago Architectural Center’s tour – “Treasures of Chicago’s Golden Age“
Willis Tower (233 S Wacker)
- This tower will always be known to me and most Chicagoans as the Sears Tower. The former Sears Tower is now the Willis Tower; so named since 2009, for a global insurance brokerage company.
On a clear day in, you can see 4 states – Illinois, Michigan, Wisconsin, and Indiana. It is the 12th tallest building in the world and is home to the highest public viewing area in the United States. The Skydeck located on the 103rd floor of the Willis Tower features the LEDGE. It is four glass boxes on the western side of the Skydeck for observing the street underfoot.
Admissions: Adult – $24.00 Child – $16.00
- Hours: 9 AM – 10 PM from March- September; 10 AM – 8 PM from October- February.
- For more information, go to the skydeck.com.
Recommendation: You will be on your feet the whole time so wear comfortable shoes. The only seating is a metal bench near the bathroom.
Chicago Loop After Hour
The Loop area empties out quickly after business hours. This time of day has always fascinated me. If you’re not used to the massive wave of people trying to get to their trains (or happen to be swimming against its current) it can be overwhelming. This is where you will see native Chicagoans at it rudest (and we’re not usually rude). Get out the way…park yourself somewhere at a happy-hour and wait until the wave passes. Here are some suggestions:
- Fisk and Co – 225 N Wabash, Happy Hour: 4 pm – 6 pm – $1 Oysters
- Berghoff – 17 W. Adams – Lower Level, Happy Hour: 4 pm – 7 pm – $4 Draft Beer, $6 Well Drinks, $7 House Wine
- Vol. 39 at Kimpton Gray Hotel – 122 W. Monroe, 2nd floor – Happy Hour: 3:30 pm – 5:30 pm
- The Bar Below – 127 S State St – Happy Hour: 4 PM – 6 PM; $4 Draft Beer, $7 Well Martinis, $6 High Balls
Restaurants in Chicago Loop
Chicago is a foodie paradise. You can get some of anything that you might have a taste for in Chicago.
- Lou Malnati’s Pizzeria (805 S. State) – Absolutely amazingly great pizza – both deep dish and thin crust.
- Yolk South Loop (1120 S. Michigan) – Great breakfast – extremely busy so prepare for a wait.
Shopping in Chicago Loop
Chicago is well known for the amazing shopping opportunities on Magnificent Mile. However, there’s a lot of great shopping in the Loop Area as well; most of it located along State Street. Read the “State Street Shopping Guide” by Choose Chicago for more information.
Chicago Loop Grocery Stores
- Trader Joe’s (1147 S. Wabash Ave)
- Jewel Osco (1224 S. Wabash Ave)
Wacker Drive – Chicago Riverwalk
I feel that that Wacker Drive/Riverwalk area deserves its own section. Wacker Drives follows the Chicago River and creates this curvy crack between the Chicago Loop and the neighborhoods north of Wacker; Streeterville, Magnificent Mile, River North, and Gold Coast.
Best Places to Stay in Chicago Downtown Wacker Drive/Riverwalk
If had to pick the absolute best part of town to stay it would be the hotels along Wacker Drive because you get to see the differences between the city that works and the city that plays. You also get to experience what Chicago is like above and below Wacker…what an adventure!
Map Hotels Wacker Drive
Wanna browse Chicago Downtown Hotels? Click here to check prices through Booking.com
Hotels on Wacker Drive Chicago
- Swissotel Chicago – 323 East Upper Wacker Drive
- Hyatt Regency Chicago – 151 East Upper Wacker Drive
- Club Quarters Hotel – 75 East Upper Wacker Drive
- Wyndham Grand Chicago Riverfront – 71 East Upper Wacker Drive
- Renaissance Chicago Downtown – 1 West Wacker Drive
Wacker Drive Attractions and Landmarks
Chicago Architecture River Tour
- This is an awesome way to view the city. I chose to use my Go Chicago Card and jump aboard the Shoreline Sightseeing “Chicago Architecture River Tour”. Use the Go Chicago Card to save money. It is a 1-hour tour of the Chicago River and the architectural landmarks that are along the river. There are 2 departure points – Navy Pier or Michigan Avenue Riverwalk (401 N Michigan Ave Plaza – look for the signs).
Recommendation: board at the Michigan Avenue location. There’s usually a long wait at the Navy Pier location.
Going to San Francisco? Not without reading “Perfect Things to Do this Weekend in San Francisco“
The Best Things to Do in Chicago: The best value for your money
- I recommend the all-inclusive Go Chicago Card pass. The all-inclusive pass allows admission to 26 tours and attractions without having to stand in long ticket lines at each attraction/tour. Download the Go Card App for easy access to your Go Chicago Pass.
Click here to purchase your Go Chicago pass.
Click here to purchase your seat on the BigBus Tour or use your Go Chicago Card for better value.
Recommendation: If you decide to sit up top, enjoy the breeze from Lake Michigan. Bring a jacket, hat, and shades just in case.
Big Bus Tour riding along State Street
- Completed in 1916, Navy Pier has been repurposed several times as a jail for draft dodgers, a training center for the U.S.Navy, and facilities for the University of Illinois at Chicago. Navy Pier has now evolved into a major tourist attraction that includes a children’s museum, a Ferris wheel, a concert venue and tons of places to eat. One day I will get the nerve to try the Ferris wheel. Well, maybe I will.
Recommendation: catch a movie at the IMAX theater or a free performance at Polk Brothers Park. Check out Navy Pier’s Calendar of Events.
Big Bus Tour leaving Navy Pier
Museum of Contemporary Arts (MCA)
- Use your Go Chicago Card (membership has its benefits) for admission into the MCA. Founded in 1957, this museum features provocative art and exhibitions meant to inspire the artist in all of us.
Recommendation: Before your visit, the MCA go online to get a heads up about the ever-changing exhibitions.
Poster Outside of MCA
The Hancock Building
- This 100 story skyscraper is the 4th largest building in Chicago. The 360 Observation Deck at the Hancock building has the TILT attraction which is a series of floor to ceiling windows that slowly tilt outside the building to 30 degrees. The charge for that is $7.00. If you pre-purchase your tickets online (which I recommend) the cost is $6.30. On my visit to the Hancock Building, I decided to skip the TILT because of the long lines. Instead, I grabbed an alcoholic beverage and found a seat to one of the best views Chicago has to offer.
On my visit to the Hancock Building, I decided to skip the TILT because of the long lines. Instead, I grabbed an alcoholic beverage and found a seat to one of the best views Chicago has to offer.
Recommendation: If you are looking for more of a chilled-out experience the observation deck has wide-wooden bleacher-like seating. Perfect for taking in the breathtaking views of Chicago.
The Robie House
- The Robie House is located at 5757 S. Woodlawn in the neighborhood of Hyde Park. The architect Frank Lloyd Wright designed this prairie-style home for a businessman by the name of Frederick C. Robie. It was completed in 1910. Mr. Wright’s vision was to build a house that was sleeker with an open space architectural design. The Robie House is the precursor to architectural modernism. Click here for tour times. You can use the Chicago Go Card to gain entry into the Robie House Tour.
Click here to purchase the Go Chicago Card.
Museum of Science and Industry
- In 1933 a building that was the Palace of Fine Arts for the 1893 Columbian Exposition became the Museum of Science and Industry It is located at 5700 S Lake Shore Drive, and not to be missed on your visit to Chicago. It is home to the largest science museum in the western hemisphere. What’s great about this museum is there’s something of interest for people of all ages.
What’s great about this museum is there’s something of interest for people of all ages. Many of the exhibits are hands-on with the intention of sparking scientific creativity within.
Exhibits range from subjects such as energy, chemistry, design, transportation, environmental science and so much more!
Recommendation: Use your Go Chicago Card to get in Click here to purchase. MSI is so huge and contains so many exhibits that you should schedule a whole day for visiting all 400,000 square feet of this museum. Don’t rush and take plenty of breaks. What’s so great about MIS is that a lot of exhibits requires sitting….thank God! My favorite is the exhibits in the Transportation Gallery.
Things to See in Chicago – Chicago Itinerary
Chicago getaway weekend itinerary
- Breakfast at Yolk South Loop, Streeterville or Marina locations
- Catch the BigBus at Hilton Chicago – Admission: Premium tickets (2 days) $49.50 for Adults, $27.00 for children. Click here for more information. It’s a great way to get a lay of the city and provides transportation to most tours and attraction. Hop on and hop off; the panoramic top-deck view is perfect for taking amazing photos of the city.
- Get off at Adler Museum
- Hop back on the Big Bus at Adler and hop off at the Museum Campus. Check out the Field Museum, Shedd Aquarium, and Soldier’s Field.
- Hop back on at Museum Campus. Hop off at Maggie Daley Park. Stroll across the park and cross Randolph Street to get lunch at Mariano’s Gourmet Grocery (333 E Benton PL). Choose to eat it at Mariano’s or if it’s not too chilly go back to Maggie Daly Park to enjoy the view and your lunch.