Chicago, located on Lake Michigan in Illinois, is among the largest cities in the U.S. famed for its bold architecture, it has a skyline punctuated by skyscrapers such as the iconic John Hancock Center, Willis Tower (formerly the Sears Tower) and the neo-Gothic Tribune Tower. The city is also renowned for its museums, including the Art Institute of Chicago.
If you have been thinking about visiting Chicago, I suggest using this guide to a plan a weekend in the city. This guide focuses on things to do during warmer months, however can be modified to fit a Winter visit. Keep reading to see what I recommend to do in Chicago, as well places to eat, drink and additional tips.
How to Get to Chicago
Since Chicago is located in the Midwest, it lies in the heart of the United States. That makes getting there a breeze, no matter how you like to travel. We personally flew from Florida to Chicago into O’Hare Airport as it had the cheapest flights with times that worked for us.
Getting there by plane
Chicago is home to two international airports conveniently located in the center of the country.
Chicago O’Hare International Airport
O’Hare airport is one of the largest airports in the world. It’s located just 16 miles from downtown Chicago and has many flight options.
Chicago Midway International Airport
Midway is located only 11 miles from downtown Chicago, however has less airlines servicing the airport. Since it’s a smaller airport, you usually (not always) move faster through it. If the flight prices are similar, Midway might be a better option.
Transportation to/from O’Hare and Midway
Both O’Hare and Midway are within easy reach of downtown Chicago.
- The Chicago Transit Authority (CTA) Blue Line ‘L’ Train, which runs 24/7, connects directly to O’Hare. The CTA Orange Line ‘L’ Train connects directly to Midway. See maps and fares.
- Taxi, Lyft, and Uber pick-up points are available at both airports.
- GO Airport Express provides shared ride services to all downtown/suburban hotels.
We chose to walk to the designated vehicle pick up area and took an Uber to our hotel accommodation.
Getting there by car
If you decide to drive, Chicago’s central location and its position as a hub for the nation’s major interstates make it a convenient drive from anywhere in the country. Chicago is accessible via several major interstates and highways: I-90 (Kennedy Expressway), I-94 (Dan Ryan Expressway), I-55 (Stevenson Expressway), I-290 (Eisenhower Expressway), and I-294 (Tri-State Tollway).
How to Get Around Chicago
Depending on what time of year you visit Chicago, the way you get around will vary based on the weather and your tolerance. I visited Chicago towards the end of Summer for Labor Day weekend and mainly got around by walking. Chicago is very walkable, however there are many other options to get around the city and I’ve listed them below for you.
The nation’s second largest public transportation system, the CTA operates Chicago’s eight ‘L’ train lines and 129 bus routes.
Train
Chicago has the “L” train. While may cities opted to put their public trains underground in order to save space, much of Chicago’s system is in fact elevated, hence the name “L.”
However, the CTA is much bigger than just the “L.” The CTA also connects suburban neighborhoods with downtown Chicago, making the morning commute much easier for many Chicago employees. Furthermore, the CTA is an extensive network that combines both rail and bus lines into a seamless system.
You can pay cash for single trip bus rides or purchase a reloadable Ventra Transit Card or Unlimited Ride Pass for both travel by “L” train and bus. Tip: Download the Ventra app to track arrival/departure times for CTA buses and ‘L’ trains, and to reload your balance on the go.
Metro Rail
The high-speed Metro commuter rail train connects outlying suburbs to downtown Chicago, and is a fast and easy way to travel to the heart of the city. Find fares and route maps.
Ridesharing & Taxis
Uber, Lyft and Taxi’s are always great options to get around the city or if you’re traveling a longer distance. I personally used Uber and Lyft in Chicago and found it very convenient.
Biking
Chicago is a very bike friendly city. There are over 200 miles of protected bike lanes throughout the city.
Divvy, Chicago’s bike-share program, offers over 580 stations and 5,800 bikes across the city, available for rent 24/7. Users simply pick up a bike from a self-service docking station and return it to a station near their destination. Find Divvy locations and rates.
Where to Stay
Chicago, the most populated city in the state of Illinois and the Midwestern United States and the third most populated city in the US, is nestled along the Great Lakes shoreline. Well-recognized for its vibrant city life, music scene (especially house music scene), shopping avenue, futuristic architecture, miles of sandy beaches, highly-distinguished colleges and universities, and prominent cultural attractions, Chicago has a gorgeous skyline that floats impressively over the banks of Lake Michigan.
We stayed at The Chicago Downtown Hotel, an Autograph Collection/Marriott Property. The location was so great for everything we had planned for the weekend. We walked mostly everywhere from our hotel and took Ubers for places that were a longer distance. I would say the majority of things you will do are within a 5-15 minute walk from the hotel. The hotel itself has a bar/lounge downstairs, staff was friendly and the room had everything we needed.
I’ve listed some of the most popular neighborhoods to help you decide where to stay in Chicago during your next visit.
Neighborhoods & Area Guide
The Loop
One of the three downtown communities of Chicago, the Loop is often the first stop for visitors traveling to the city. Neighbored by the Chicago River to its north and west and Lake Michigan to the east, the neighborhood is home to the tallest structures that comprise Chicago’s magnificent skyline.
Recommended for: All kinds of travelers
Other Highlights: Museum of Contemporary Photography, Millennium Park, Vietnam Veterans Museum, Chicago Architecture Foundation, and Cloud Gate.
Hyde Park
One of the most prominent neighborhoods in Chicago, Hyde Park is located on the south side of the city, along the south lakefront. The biggest attraction in the neighborhood is central Hyde Park, home to the revered University of Chicago. Dotted with interesting bookstores, great museums, budget street food, and tree-lined streets, Hyde Park houses the Museum of Science and Industry, Oriental Institute Museum, and Robie House.
Recommended for: All kinds of travelers.
Other Highlights: Drexel Fountain, The National House, Jackson Park, Midway Park
Lincoln Park
This neighborhood is a mix of college students and young families. Lincoln Park is home to significant attractions such as Lincoln Park Zoo, DePaul University, and St Michael’s Church.
Recommended for: All kinds of travelers
Other Highlights: Chicago History Museum, Lincoln Park Conservatory,
Magnificent Mile
The shopping central of Chicago, Magnificent Mile is the city’s elite commercial district. Also known as the Mag Mile, this neighborhood is lined with mid and high-end stores making it the perfect place for any shopaholic!
Recommended for: All kinds of travelers
Other Highlights: 360 Chicago Observation Deck
Near South/South Loop
Home of many Chicago landmarks, Near South is among the oldest settlements in the city and was once considered the most prestigious. After a few decades of inactivity, the area has once again emerged as a tourist hotspot filled with several activities and attractions. The Museum Campus is home to three of the finest natural science museums in the country while McCormick Place serves as a gigantic convention center.
Recommended for: All kinds of travelers
River North
River North is known to house the largest concentration of art galleries in the country, outside of Manhattan. The neighborhood is also home to several fine-dining restaurants, lively bars, interesting entertainment venues, and famous nightclubs.
Recommended for: All kinds of travelers
Other Highlights: Navy Pier, Tribune Tower, Chicago Children’s Museum
Gold Coast
This historic district, located in Chicago’s Near North Side community area, is one of the most high-end neighborhoods in Chicago. The upscale neighborhood boasts several skyscrapers, row-houses, majestic mansions, specialty boutiques, and Michelin-starred restaurants. Oak Street is the area’s designated shopping street while Rush Street is where you head for the best nightlife in the district.
Recommended for: All kinds of travelers, especially those seeking luxury.
West Loop/Near West Side
Near West side is home to a number of Chicago’s cultural landmarks, including the Blues Brothers, the deep-dish pizza, the blues, and the Chicago-style hot dog. The neighborhood also comprises the West Loop, which has many elite restaurants and a few museums. If you are here for the weekend, don’t miss a visit to the New Maxwell Street Market.
Recommended for: All kinds of travelers, especially foodies
What to Do
Riverwalk
The Riverwalk is the center of socializing for Chicago, especially on the rare warm summer days. Each section has a different theme as well as cocktail bars. The cocktail bars are a bit expensive, but you can’t pass up a cocktail with these incredible views and atmosphere.
Visit a Museum
Here, our list of the best museums in the Windy City
- The Museum of Contemporary Art Chicago
- Shedd Aquarium
- Museum of Science & Industry
- Field Museum of Natural History
- WNDR Museum
- Art Institute of Chicago
- Illinois Holocaust Museum
- Robie House
- Chicago Children’s Museum
Visit Cloud Gate
Go say hi to the Bean first in the morning to beat all the crazy crowds. If you didn’t go to the Bean, did you even go to Chicago? The Bean is actually officially called “Cloud Gate,” and was created by an Indian-born British artist named Anish Kapoor. It is made up of 168 stainless steel plates which were welded together and polished so that there were no visible seams. It gets its nickname from its iconic kidney bean-like shape.
Visit Millennium Park
Located in the heart of Chicago in the Loop, Millennium Park is a 24-acre urban park that is home to several of the city’s top attractions and therefore is a must during your 2 days in Chicago. The park opened in 2004 – but it gave new life to the city.
SkyDeck
You will definitely feel like you’re on top of the world as you look out into the city and beyond (on a clear day, you can see a view of four states) from the 103rd floor of the Willis Tower, aka the second tallest building in the Western Hemisphere. Purchase tickets here.
EXPLORE NAVY PIER
Navy Pier is iconic, complete with amazing views of the city and Lake Michigan, the Ferris wheel, shops, restaurants, and more! The Crystal Gardens and Miller Lite Beer Garden are some great spots to check out while there!
Visit a Rooftop
Chicago is filled with amazing views of the city and it’s definitely worth visiting a few rooftops during your visit. Chicago is not only home to the largest rooftop bar in the world and some great rooftop pools, but buzzing with vibrant and trendy rooftop lounges, offering views over both the Chicago skyline and Lake Michigan.
- Cindy’s – features sweeping views of Millennium Park, “The Bean”, Michigan Avenue, and the lake. Enjoy a drink on the outdoor terrace, then step inside the soaring, glass-enclosed dining area for elevated comfort food and more handcrafted cocktails.
- Roof on theWit – Young professionals cut loose after a long week of work at this lively rooftop lounge on the 27th floor of theWit hotel. With its modern design, glittering city views and nightclub atmosphere.
- Aba – It feels like summer all year long at Aba, with its abundant greenery and a light-and-airy atmosphere. Serving Mediterranean cuisine, this rooftop is worth a visit.
- OffShore Rooftop – located in Navy Pier area, this rooftop bar is the nations largest rooftop venue and offers panoramic views of lake Michigan and the city skyline. The space is 36,000 sq ft with entertainment and gaming.
- Utopian Tailgate – Utopian Tailgate is Chicago’s newest never-ending rooftop partyscape. Dreamy décor and interactive fun and games greet you at our 300-person 10,000-square-foot, indoor/outdoor never-ending tailgate. Putterball, super-sized Jenga, Plinko, drinking games, disco dance party, and a whole lot more mix with elevated eats and whimsical whistle-wetters all year ‘round.
- LH Rooftop – Having appeared in popular online guides from Time Out and Thrillist, LH Rooftop at London House Chicago is no doubt an absolute gem. It is located on the 21st (indoor) and 22nd (outdoor) floors and offers panoramic views overlooking Chicago River and Michigan Avenue. Although more on the expensive and luxurious side, it’s certainly quite the experience sipping on a glass of bubbly here.
- The Signature Lounge – located on the 95th floor of the John Hancock building offering 360 views of the Chicago skyline.
Architecture Tour
The breeziest way to survey the city’s famed architecture. An architectural tour is a must for any visit to Chicago, and the Chicago Architecture Foundation employs certified volunteers who narrate the history behind 50-plus downtown buildings. Tours are located on the Chicago Riverwalk and last about 90-minute tour. Full-service cash bar on board too!
Visit the Theatre District
The Chicago Theatre District is a hub for world-class productions and premieres, particularly at the district’s three Broadway In Chicago theatres:
- CIBC Theatre, which first opened as a vaudeville theatre in 1906
- James M. Nederlander Theatre, a lavish movie palace from the early 1900s
- Cadillac Palace Theatre, an ornate venue designed by legendary theatre architects and inspired by Versailles
You can do dinner and a show or just stroll the area and take pictures!
Stroll the 606
A formerly abandoned stretch of elevated railway track named after the first three digits in every Chicago zip code. The 606 is a convenient way to get between Logan Square, Humboldt Park, Wicker Park and Bucktown. The 2.7-mile path was spruced up by the city and turned into a functional attraction that delights locals and visitors—just remember to keep moving
Where to Eat
- Etta – Neighborhood hot spot with a locally sourced New American menu of wood-fired fare & brunch plates.
- Enoteca Roma – Italian cuisine in a beautiful outdoor hidden patio. Located in Wicker Park.
- Summer House Santa Monica – Sunny restaurant serving New American grub, tropical drinks & more in an airy space with an atrium. Click here for menu.
- The Hampton Social – The Hampton Social opened its flagship location in the bustling River North neighborhood of Chicago in August 2015. The 7,000 sq ft. lifestyle concept is a dining hotspot that evokes East Coast living in every aspect – from the white-washed, nautical walls to the signature seafood fare. Click here for menu.
- Time Out Market – Time Out Market Chicago, a culinary and cultural destination in the heart of Fulton Market. The 50,000-square-foot space houses multiple kitchens, three bars and one drop-dead gorgeous rooftop terrace—all spread across three floors.
- Portillo’s Hot Dogs – It would be a shame not eat a Chicago dog while visiting! The chain has been a Chicago mainstay for over 50 years, and serves up the juiciest, most flavored packed hot dog you’ll find on your trip to Chicago.
- Celeste – located in River North, this restaurant serves light bites, cocktails and music. Swanky hangout with a downstairs bar plus a lounge & art deco New American supper club upstairs.
- The Purple Pig – Mediterranean restaurant with amazing cuisine and highly recommended restaurant in Chicago. Click here for menu.
- RPM Italian – presents cuisine that is modern in approach and Italian in spirit, with dishes intended to be shared. Sophisticated and chic, yet unpretentious, RPM Italian is perfect for a great meal.
- Au Cheval’s – famous burger has received many, many accolades, including being declared one of the best, if not the best burger in the US. So obviously, it is also one of Chicago’s most popular restaurants, and people wait up to three hours for a taste of that burger.
- Shore Club – Mediterranean cuisine overlooking views of Lake Michigan. The Shore Club makes you feel like you’re in Miami with it’s beach side vibes.
- The Dawson – Located in Chicago River West serving American cuisine and crafted cocktails. Great outdoor seating.
- Monteverde – Stylish spot serving refined, contemporary Italian fare such as fresh pastas, plus global wines. This restaurant was outstanding and my favorite meal of the trip. Make reservations in advance. Click here for menu.
- Beatnik – located on the river, this beautiful restaurant serves Mediterranean cuisine in a stunning ambiance. Gorgeous patio, make reservations in advance.
- Pizzeria Portofino – located in Riverfront and serving up Italian cuisine. The restaurant is beautifully decorates and makes you feel like you’re in Italy. The views overlooking the river are stunning. Request a table outside.
WHERE TO EAT DEEP DISH PIZZA?
Giordano’s – Giordano’s serves up a solid deep dish, and has the perk of having multiple locations that are close to some popular attractions, such as Millenium Park, the Magnificent Mile, and Navy Pier.
Lou Malnati’s – Lou Malnati’s is a crowd favorite of both tourists and locals alike, and it’s easy to see why – the deep dish here is simple yet authentic, and definitely satisfying. Lou Malnati started as one single location in 1971, but has since expanded to over 50 locations so chances are you’ll find one that is convenient to you!
Pequod’s – Pequod’s has long been a favorite of locals, and since it still only has 2 locations, it still has that neighborhood pizza joint vibe. And the deep dish is to die for! What sets Pequod’s apart is the signature “halo,” which is created by sprinkling cheese edge to edge to create a crisp, brown rim on the outside.
SHOP MY POST
Have you ever been to Chicago or is it on your bucket list? Feel free to share your thoughts in the comments or any questions.
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