Everyone knows that Chicago is one of the best destinations in the Midwest. And with this 3-day Chicago itinerary, I’m sharing some of the best of the Windy City plus some hidden gems that you probably won’t find anywhere else.
Why? I have lived here for decades and can open your eyes to more than The Bean in Millenium Park, Navy Pier, and the Magnificent Mile.
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Side note: The following post was written by Tanya, a local of Chicago. This way, you can be sure you are reading the best and most accurate weekend in Chicago itinerary. Locals know best! See the author’s bio at the end for more information.
Table of Contents
How do I get to Chicago?
To reach Chicago by air you’ll need to reserve a flight to either O’Hare International Airport (ORD) or Midway International Airport (MDW).
Local Tip: Don’t rent a car, the public transportation system in Chicago is extensive and efficient. Most points of interest are within walking distance or near a train station and you will save dollars on parking which starts at $35 per day.
Bus services like Greyhound and Megabus offer routes to Chicago. The bus journey is suitable for trips under 4 hours. It is a budget-friendly choice compared to flying.
Alternatively, you can opt for a train ride to Chicago. Amtrak runs long-distance train services to the city. Traveling by train is comfortable and eliminates the hassle of driving.
When is the best time to visit Chicago?
Chicago’s location in the Midwest gives you a fantastic chance to enjoy all four seasons to the fullest because of year-round activities.
Summer weather is hot and sometimes sticky. But there are lots of famous festivals like Lollapalooza, and the Taste of Chicago, as well as neighborhood events.
Spring and Fall are excellent times to visit, especially if you want to avoid the peak tourist crowds. You can often find great deals on hotels and activities during these shoulder seasons. Just be prepared for cooler or rainy climates and follow recommendations on how to dress in Chicago.
Where should I stay in Chicago?
Chicago is a melting pot and the various neighborhoods represent a diverse culture of people from around the globe.
If you truly want to experience the culture of Chicago, I recommend that you stay in a neighborhood like Old Town, Lincoln Park, Wrigleyville, or Ukrainian Village.
However, if you want to be on the beaten path with proximity to the well-known iconic landmarks of Chicago, then you should stay closer to the Loop in neighborhoods like River North, Fulton Market, or the nearby South Loop.
Chicago has a range of hotels that make it affordable for any price point, from hostels to 5-star accommodations.
Chicago Hotel Recommendations:
- Budget-friendly Option: Freehand Hotel is a mixture of private and shared spaces. The rooms are small with basic amenities, but they will make for a good night’s rest.
- Mid-range Option: Embassy Suites Magnificent Mile is one of my personal favorites and it is my first choice for a family staycation. If you are familiar with this brand of hotel, they offer free, made-to-order hot breakfasts and a manager’s reception with complimentary cocktails and snacks. This hotel is perfectly situated for popular attractions in Chicago.
- Luxury Option: Four-Seasons Hotel Chicago has exceptional service as one would expect from lux accommodations. It’s a great option for celebrating special occasions or a romantic getaway.
- Dog-friendly Stay: Stay Pineapple, The Loop Chicago- OK, I left out the part about this being an iconic hotel. But, not just the hotel, the entire building is a National Landmark! The hotel is in the Reliance Building which has great architectural significance in Chicago and they are fur-baby friendly.
- Unique Option: The Palmer House– I personally love this hotel because it has a rich history and feels European. It’s also known as the place where brownies were invented. It’s one of the stops on the Chicago walking tour so even if you don’t stay, it’s worth taking a stroll through the lobby.
3-Days in Chicago Weekend Itinerary
I am super thrilled to share this itinerary for you to see another side of Chicago through its neighborhoods! Here’s exactly how I would spend 3 days in Chicago.
Day 1: Touristy Fun
Although we are going to go off-the-beaten path during these 3 days in Chicago, I do believe some of the touristy stops are worth it for first-time visitors. Day 1 is the perfect time to check these off the list!
Morning
Start the morning with Chicago’s Hop On/Hop Off bus tour. You will get some incredible shots of the city, and you’ll see a ton of landmarks in a short amount of time. The bus tour starts at 98 E Wacker Dr and has 13 stops along the way. There’s an automated recording going during the tour to give you a bit of comedy and fun facts about the city.
Get off at the Millenium Park stop to check out the famous Bean. Take some time to wander around the park and people-watch a bit. Then hop back on the bus and continue along the route.
Book your Chicago Bus Tour Here!
Afternoon
Next, hop off the bus at the Chicago Museum Campus and walk to the Shedd Aquarium. This massive aquarium is home to over 30,000 different animals…including the beloved beluga whales!
Tip!! Admission to the Shedd is included in the Chicago City Pass. You can save up to 48 percent on 5 of the top attractions!
Alternatively, enjoy the afternoon at the Art Institute of Chicago. It is a number one tourism spot and we’re proud of that! Or, if you’d rather shop, let your feet guide you along State Street or the Magnificent Mile.
Evening
Now it’s time to relax a bit aboard a sunset cruise to enjoy the golden hour. This 90-minute architectural cruise takes you on a peaceful journey down the Chicago River while giving you a background of the design and construction of over 50 of the most famous buildings.
If you STILL have more energy, you can end your first night in Chicago with a trip to the Sky Deck for the best views of the night skyline. If you have it in the budget, you can even indulge in a Chicago-style pizza on the 103rd floor.
If a dinner in the sky is not in the budget, no worries! There are plenty of other options in the city to grab a deep dish! I recommend Lou Malnati’s Pizza on Wells Street.
Book your Chicago City Pass here!
Day 2: Explore Chinatown
Morning
Ready for a cultural trip through Chicago? Grab a light breakfast to go and then catch the red line and head south to the Chinatown stop. The ride from the loop is less than 20 minutes.
You may be stuffed from the tour, but don’t worry, there are plenty of opportunities to walk it off on Cermak Street, Wentworth Street, or the nearby square. There are tons of family-friendly activities in Chinatown.
Be sure to check out the Nine Dragon Wall and then take a stroll around Ping Tom Memorial Park.
Afternoon
You can’t visit Chinatown and not sample some of the delicious foods and there’s no better way to do it than a Chinatown Food Tour. A guide will take you to all the best spots with samples at each!
Evening
Head back to Ping Tom Memorial Park to catch the water taxi at the pagoda back to the center of Chicago. It’s a great and inexpensive way to see Chicago from another perspective. Just note that the water taxi does not run year-round, it is closed in the winter season.
Then grab dinner at The Purple Pig. Although this spot is a bit pricey, it’s great for indulging in rich foods like pork belly, duck, and braised shoulder. This place is always buzzing because the dishes are that good!
Day 3: Take a Trip to Little India
Morning
Today, I’ll show you how to explore Roger’s Park, a neighborhood on the north end of Chicago.
After breakfast, take the CTA Red line north to the Loyola stop, walk 5 minutes south to Devon Avenue, then take the #155 bus to Western Avenue for a cultural immersion of “Little India”.
The street is dotted with restaurants, boutiques, salons, markets, and places to shop for spices, snacks, jewelry, and souvenirs. It will take about two hours to peruse the stores.
Don’t miss the Tahoora Sweets & Bakery for some Indian treats. It will keep you fueled and pairs nicely with a mango smoothie from Annapurna.
Afternoon
If you have time to stop for lunch to enjoy Indian cuisine, it doesn’t get more authentic than this neighborhood. There are MANY choices to choose from.
After lunch, you can stop in one of the salons for a henna application. Just be sure to make an appointment in advance.
Henna is used for its aesthetic value and as a form of artistic expression. Intricate henna designs on the hands or feet are considered beautiful and a way to show creativity. And if you are traveling with teens or younger ones, they will love it!
Then, head back to the Loyola train station (don’t forget to catch the bus on Devon).
Evening
End your 3 days in Chicago with a stroll along the Chicago Riverwalk and finish your Indian-themed day experience with dinner at a downtown restaurant like Indian Garden Restaurant or Cumin Club.
3 Days in Chicago Map
Here’s a quick recap and map to help you plan you Chicago weekend getaway!
- Day 1: Hop on and off Bus tour, The Bean, Shedd Aquarium, Sunset Cruise, Skydeck
- Day 2: Chinatown, food tour, dinner at The Purple Pig
- Day 3: Roger’s Park, Henna Tattoo, Chicago Riverwalk
Other Things to do in Chicago:
It’s no secret that Chicago is jam-packed with exciting things to do. Although you won’t be able to fit in everything during your Chicago weekend trip, you may want to switch some things around in the above itinerary. Here are some fun ideas!
- Explore The Art Institute of Chicago: One of the oldest and largest art museums in the United States, The Art Institute of Chicago houses an impressive collection of artworks spanning thousands of years and diverse cultures. From Van Gogh’s “The Bedroom” to Grant Wood’s “American Gothic,” art lovers will find plenty to admire here.
- Catch a Show at The Second City: Experience the world-famous comedy scene at The Second City, where legendary comedians like Tina Fey, Steve Carell, and Bill Murray got their start. Enjoy improvisational comedy performances or take a comedy writing or improvisation class to tap into your comedic talents.
- Visit The Field Museum: Delve into natural history and cultural artifacts at The Field Museum, where you can encounter Sue, the largest and most complete Tyrannosaurus rex skeleton ever discovered, as well as ancient Egyptian mummies, and exhibits on dinosaurs, Native American cultures, and more.
- Take a Walk along the Lakefront Trail: Enjoy breathtaking views of Lake Michigan and the city skyline as you stroll, jog, or bike along the scenic Lakefront Trail. Stretching for miles along the lakefront, this picturesque path offers a refreshing escape from the hustle and bustle of the city.
- Shop on the Magnificent Mile: Explore the upscale shops, boutiques, and department stores along North Michigan Avenue, known as the Magnificent Mile. From luxury brands to designer boutiques and flagship stores, this premier shopping destination offers something for every style and budget.
- Experience Chicago’s Blues Scene: Immerse yourself in the soulful sounds of Chicago blues at legendary clubs like Buddy Guy’s Legends, Kingston Mines, or Rosa’s Lounge. Enjoy live performances by talented musicians and feel the rhythm of this quintessential Chicago music genre.
- Three Dots and a Dash: Chicago has several speakeasies, so if you and your tribe are up for finding the front door, head over to this tiki bar. It’s tucked away in an alley and serves great food and drinks.
Where to Eat in the City:
It’s no surprise that Chicago is a foodie town. The city is filled with renowned Michelin-star restaurants as well as hole-in-the-wall spots that can draw crowds. Here are some of my favorite places to eat in Chicago!
- Gino’s East (Pizza)
- Giordono’s (Pizza)
- Pizano’s (Pizza) Psst: Die-hard pizza fans should sign up for a Chicago Pizza tour.
- Food Revival (Food Hall)
- UrbanSpace (Food Hall)
- TimeOut Market (Food Hall)
- Chicago French Market (Food Hall)
- Tank Noodle (Vietnamese)
- Iyanze Bar and Cafe (West African)
- Furama (Chinese)- I HIGHLY recommend this spot for some dim sum!
Other Tips to Know BEFORE Visiting Chicago:
- Weather: Chicago’s weather can be unpredictable (it is the Midwest after all), with hot and humid summers and cold winters. Be prepared for sudden changes in weather by dressing in layers and checking the forecast before your visit.
- Public Transportation: Chicago has an extensive public transportation system, including buses and the “L” train (elevated/subway). Consider using public transportation to navigate the city efficiently, especially during peak traffic times.
- Explore Neighborhoods: As this 3-day Chicago itinerary suggests, Chicago is a city of diverse neighborhoods, each with its own unique character and attractions. Take the time to explore off the beaten path!
- Safety Precautions: While Chicago is generally a safe city for tourists, it’s essential to exercise caution, especially in busy tourist areas and at night. Stay aware of your surroundings, avoid displaying valuables, and stick to well-lit and populated areas.
- CityPass: Consider purchasing a CityPass to save money on admission to top attractions like the Shedd Aquarium, Skydeck Chicago, and the Field Museum. The CityPass also includes discounted public transportation options.
- Festivals and Events: Check the city’s event calendar for festivals and events happening during your visit. From the Taste of Chicago food festival to the Chicago Jazz Festival, there’s always something exciting happening in the city.
Author’s Bio:
Tanya is a freelance writer and content creator of Travels & Treasures. She has lived in Chicago for over 30 years and has visited 43 of the 50 United States, France, Italy, Spain, Portugal, and the UK. She writes to guide your next adventure to hidden gems or top tourist sights in Chicago and abroad.
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