Chicago is perfect for a fun-filled weekend getaway or longer trip! There are so many things to see and do in Chi-town (and amazing food)! We’ve compiled some of our favorite activities to help plan your next Chicago trip.
The beautiful state of Illinois is known for its farmlands, forests, rolling hills and wetlands, but Chicago brings big city vibes to this northeastern state.
Bordering Lake Michigan, Chicago is among the largest cities in the United States. Hosting bold architecture and a killer skyline views, the windy city makes for a great vacation destination!
There are many aspects to a getaway that work to either make or break the overall experience. Between accommodations, food, entertainment, and travel, if even one element isn’t up to par, you’re likely to get hung up on it and it could very well spoil your entire vacation. Don’t let this happen to you! Read up on your destination and see what options are available for your trip.
Chicago is an ever-growing city that has so much to offer travelers, but which activities will be the best crowd pleasers for your trip?
Our TMMH Team has put together our favorite Chicago tips to help you plan the perfect weekend trip. So, if a visit to the windy city is on your bucket list, you won’t want to miss these great attractions!
- Best Hotel Options in Chicago
- The Langham Chicago
- Hotel EMC2, Autograph Collection
- Hilton Chicago O'Hare Airport
- Peninsula Chicago
- Virgin Hotels Chicago
- Best Things to See and Do in Chicago:
- Must-see Chicago Attractions
- Chicago Natural Attractions to see
- Annual Events and Fun for Chicago
- More Chicago Heritage Attractions
- The Best Restaurants to Visit on a Chicago Trip
- How to get Around Chicago
- Arriving to Chicago
- Transportation Within Chicago
- Final Thoughts on a Perfect Chicago Weekend Trip
- Keep Reading for more Great Weekend Travel Tips
Best Hotel Options in Chicago
You need a comfortable place that is easily accessible to all of the activities and will ensure you’re able to rest at the end of your busy tourist day, which is why your choice of hotel is so important.
Chicago is a vibrant city filled with world-renowned attractions, from Millennium Park’s iconic Cloud Gate and Crown Fountain to the bustling shopping district along Michigan Avenue. Staying in a hotel within walking distance of these sites is ideal, as it allows you to experience the city up close.
Here are some of the best hotels in Chicago that have great amenities and are located in the heart of the main action. For travelers who only have a short time we are including the Hilton at the O’Hare International Airport because it has easy access to downtown via the CTA blue line trains.
The Langham Chicago
Address: 330 N Wabash Ave, Chicago, IL 60611
Why this Chicago hotel is worth considering:
The Langham is a very elegant option. It is a modern skyscraper designed by Mies van der Rohe. The location along the Chicago River makes it ideal for both river views and riverwalk access. It’s also only a 5 minute walk from the Magnificent Mile, and a 10 minute walk to the historic Wrigley Building and Tribune Tower.
Hotel EMC2, Autograph Collection
Address: 228 E Ontario St, Chicago, IL 60611
Why this Chicago hotel is worth considering:
This beautiful hotel combines art and technology, creating an experience that is both innovative and whimsical. It is only two blocks from Michigan Avenue and provides easy access to premier shopping, the Museum of Contemporary Art, and Navy Pier. Their restaurant, The Albert, also serves up whimsical scientific dishes. The rooms at EMC2 include smart tech and unique designs making this hotel perfect for travelers who appreciate a creative atmosphere alongside convenient walking access to top activities.
Hilton Chicago O’Hare Airport
Address: 10000 W O’Hare Ave, Chicago, IL 60666
Why this Chicago Hotel is worth considering:
This convenient hotel is located inside the O’Hare International Airport. It is perfect for when you only have a short time in the city! We recently stayed here for one night (then had a flight the next evening) and were able to see and do everything that we wanted in the city easily. It is not walking distance to the city, but its best feature is its proximity to the CTA Blue Line. The Blue Line runs directly from O’Hare to downtown Chicago, making it easy to reach the city center and return. We took the Blue Line to the Washington Street stop then walked to Millennium Park and the Navy Pier from there. The hotel offers soundproof rooms and balconies with a great view of the runway at ORD. Overall, it is ideal for those wanting convenient access to both the airport and Chicago’s attractions.
Peninsula Chicago
Address: 108 E Superior St, Chicago, IL 60611
Why this Chicago hotel is worth considering:
The Peninsula Chicago ranks as one of the top hotels in the city. It is known for its many amenities, large rooms, and a focus on service. It’s located near Water Tower Place. This means your steps away from the John Hancock Center and the Chicago Water Tower. Peninsula has a stunning rooftop terrace and spa as well! The central location makes it ideal for shopping, dining, and sightseeing along the Magnificent Mile.
Virgin Hotels Chicago
Address: 203 N Wabash Ave, Chicago, IL 60601
Why this Chicago hotel is worth considering:
Virgin Hotels Chicago has a trendy, boutique feel. It’s located near Millennium Park and the Chicago Theatre. It’s known for its iconic “Chambers” (rooms) and a modern feel. The hotel also features the Commons Club which is great for dining and cocktails. There is an amazing rooftop bar, Cerise, that boasts wonderful views of the skyline. From here, you can easily walk to the riverwalk, Michigan Avenue, The Cloud Gate (bean) sculpture, and other nearby landmarks.
Other Great Hotel Contenders: The Blackstone, Four Seasons Hotel Chicago, and Londonhouse Chicago Hilton Curio Collection
More options to find the perfect Chicago hotel for your trip:
Booking.com
Best Things to See and Do in Chicago:
The main reason to travel is to experience and see new things. These sights and activities allow Chicago visitors to acquire new insights and better understand the area in which they’re exploring.
A great way to save money and get entry into many attractions in Chicago is to get the Chicago City Pass that includes tickets to different experiences in the windy city!
Must-see Chicago Attractions
The Art Institute of Chicago – Located in the Loop area at 111 S. Michigan Ave. (Modern Wing at 159 E. Monroe St) – It is definitely worth a visit! It is also close to the Crown Fountain at Millennium Park.
Millennium Park & Cloud Gate(The bean) – This famous park is a must-do and there is so much to see! You can enter from Michigan Ave and Washington St. or Madison St. -Download a Free public art self-guided tour here. Our favorite thing to do here is to have a burrito at Casa Bonita just across from the Cloud Gate sculpture and people-watch!
The Crown fountain by artist, Jaume Plensa, is also mesmerizing to watch because it changes every few minutes to a different face that incorporates the water stream from the fountain. It is also a great people-watching spot to just sit and relax.
Chicago Riverwalk – This is another must-do area with 1.25 miles and 4 districts filled with places to eat and drink, museums, as well as water activities like kayaking. Try out the Gourmet dinner cruise that elegantly brings diners down the river with a jazz backdrop and great food.
Wrigley Field – A classic must-do for baseball fans! Catch a baseball game at this famous stadium or just tour the grounds.
Field Museum of Natural History – A great museum for science, dinosaurs, artifacts, culture! If you have more than a day, you can spend several hours here.
Skydeck Chicago – Willis Tower – There is a glass balcony observation deck called, The Ledge, with beautiful and terrifying views from the 103rd floor deck!
Lincoln Park Zoo – The zoo was founded in the 1800’s and is a very well-established zoo worthy of a visit if you have time.
Shedd Aquarium – Very close to the Field Museum and on the Lakefront. It is easy to visit a few of these close-by locations in a day.
Chicago Navy Pier – Your could spend a whole day here with all of the amusement rides, eating places, Children’s Museum, and theater or just sit on the water and watch the boats go by. It is located in the Streeterville area of Chicago on Lake Michigan.
Buckingham Fountain – Beautiful fountain in Grant Park at 301 S. Columbus Drive usually open May-October
The Magnificent Mile – Great shopping and posh area located on the North end this area includes luxe shopping, famous buildings like the Hancock as well as many restaurants.
The Crown Fountain on the edge of Millennium Park is mesmerizing and you can sit here to watch it change faces and transform.
Chicago Natural Attractions to see
- Montrose Point – Beautiful and natural bird santuary in the city! 4400 N Simonds Dr.
- Chicago River – Famously dyed green for St. Patrick’s Day, this river is located in between Navy Park and Millennium Park emptyng into Lake Michigan (The Riverwalk runs along the Chicago River)
- Lakefront Trail– 18 mile pedestrian and bike trail along Lake Michigan located from Ardmore Ave. on the north to 71st St on the south side.
- Lincoln Park Conservatory – 2391 N Stockton. They have beautiful holiday displays and don’t miss the orchid section!
Annual Events and Fun for Chicago
- Lollapalooza (July/August) Lollapalooza is a four-day music festival held annually in Chicago’s Grant Park. With a diverse lineup of popular artists from various genres, art installations, and food vendors, Lollapalooza offers an unforgettable experience for music lovers and festival-goers alike.
- Chicago International Film Festival (October) The Chicago International Film Festival showcases the best in independent and world cinema every October. With screenings, panel discussions, and workshops, the festival aims to introduce audiences to diverse films and filmmakers while promoting creativity and cultural understanding.
- Chicago Architecture Biennial (September) The Chicago Architecture Biennial, held every two years, is a celebration of architectural innovation and design. The event features exhibitions, installations, and educational programs, providing an opportunity for both professionals and enthusiasts to engage with the latest trends and ideas in the world of architecture.
- Chicago Jazz Festival (Labor Day weekend) The Chicago Jazz Festival is a 4-day celebration of Jazz at Millennium Park Labor Day weekend. The event features musicians and artists from around the globe, offering attendees a chance to explore diverse musical styles and cultures through live performances.
To find current events running and offered at your time of travel check Events Calendars with: Choose Chicago, Time Out, and or Your Chicago Guide.
More Chicago Heritage Attractions
- Garfield Park Conservatory – One of the largest offering many activities.
- Holy Name Cathedral– 735 N. State St. – Amazing gothic revival architecture and is definitly worth seeing.
- Frank Lloyd Wright’s Frederick C. Robie House – Located near the University of Chicago at 5757 South Woodlawn Ave.
The Best Restaurants to Visit on a Chicago Trip
Chicago has a happening culinary scene, from deep-dish pizza and Chicago-style hotdogs to globally inspired dishes in unique, trendy settings. We’ve added our favorites in a list of must-visit restaurants that offer authentic Chicago flavors or trendsetting dishes in amazing atmospheres. Whether you are a foodie traveler or just want to try Chicago cuisine, you’re going to sit down and eat something, so you might as well use eating as an opportunity to further explore and discover the local area and culture. You also just have to try Chicago deep-dish pizza and a dog!
Harry Caray’s Italian Steakhouse
Address: 33 W Kinzie St, Chicago, IL 60654
This legendary restaurant was named after the iconic Chicago Cubs announcer, Harry Caray’s Italian Steakhouse is a must-visit for sports fans and lovers of authentic Italian-American cuisine. It is known for its dry-aged steaks and Italian-inspired dishes, it’s also a popular spot for locals and the bar area fills up quickly. We visited here on our Chicago Gangster Food Tour and loved it!
The Girl & the Goat
809 W Randolph St, Chicago, IL 60607
This restaurant was created by celebrity chef Stephanie Izard. The Girl & the Goat is famous for its creative, globally inspired small plates and vibrant atmosphere. It’s in the West Loop area. The menu favorites include roasted pig face and goat empanadas, along with a range of seafood and vegetarian options. The eclectic flavors and ambiance make this a perfect foodie stop!
J’s Dawgs N Burgers
1001 N Winchester Ave1810 W Taylor St, Chicago, IL 60612
You can’t visit Chicago without trying a Chicago-style dog. J’s-Dawgs is the place to go for an authentic experience. Located in Little Italy, J’s-Dawgs serves up hotdogs loaded with classic toppings: yellow mustard, bright green relish, chopped onions, tomato wedges, a pickle spear, peppers, and a dash of celery salt. It was highly recommended on our Chicago food tour and we agree that it was the best!
Au Cheval
2537 N Kedzie Blvd
They are known for having one of the best burgers in America, Au Cheval is an upscale diner with loyal customer. It’s located in the trendy West Loop area. This is the place to go if you’re in the mood for an amazing double-stacked cheeseburger with all the fixings. The burger is served with a thick-cut slab of bacon, fried egg, and homemade pickles. The vibe is cool and vintage-inspired and the drinks are worth a try too.
Alinea
Address: 1723 N Halsted St, Chicago, IL 60614
An unforgettable fine-dining experience option, Alinea is one of Chicago’s most renowned restaurants, known for its innovative, multi-course tasting menus and avant-garde presentations. Head chef Grant Achatz, has helped Alinea earn three Michelin stars and delivers a unique journey through modernist cuisine. Each dish is artfully designed and presentedt.Reservations are a must and it’s a bit of a splurge, but for food lovers, Alinea is must-try.
Pizzeria Uno and Pizzeria Due
619 N Wabash Ave, Chicago, IL 60611 (Uno) and 619 N Wabash Ave, Chicago, IL 60611 (Due)
This was our first place to try Chicago deep dish and it is our favorite! Known as the birthplace of Chicago-style deep-dish pizza, Pizzeria Uno and its sister location, Pizzeria Due, serve some of the city’s most iconic pies. It was established in 1943, Pizzeria Uno created the deep-dish pizza with its thick, buttery crust and layers of cheese, chunky tomato sauce, and toppings. The location near the Magnificent Mile makes it a perfect place to visit. We think both locations are essential stops for anyone wanting a true taste of Chicago’s deep-dish legacy. There is always a wait, but the pizza is well worth it.
Other Great Foodie Contenders: Carnitas Uruapan, Daisies, and J.P. Graziano Grocery.
How to get Around Chicago
Getting around Chicago is a major consideration to make sure you get to see everything on your itinerary! We used the CTA blue line trains as well as just walking to each destination, but it’s really easy to just get an Uber or Lyft too. Driving is more difficult because of parking options.
We also used one of the motorized tuk tuk bike taxis to get from Navy Pier back to Millennium Park and it was well worth it to save our legs after walking all day!
Arriving to Chicago
Planes: If you plan to fly into Chicago for your vacation it would be done through either O’Hare International Airport or Midway International Airport.
Trains: You can roll into Chicago Union Station by rail. We’ve been on Amtrak’s Crescent from New Orleans here.
Automobiles: Of course, you also have the option of driving your own vehicle to your destination (traffic was crazy in Chicago on our last visit). If this is your plan you will want to check your hotel’s parking availability or locate a parking facility nearby.
Transportation Within Chicago
Once in Chicago you have many options for transportation to get you to and from your varied destinations:
- Metra Rail
- Taxis [using CHICABS, ARRO, or CURB]
- Buses – We love the Big Bus Hop on hop off because it can get you to many locations and give info on each on the way.
- Ridesharing such as Lyft or Uber
- Water Taxi [Chicago Water Taxi or Shoreline Water Taxi]
- Shuttles and Limo Services
- Biking or Bike Rentals
- Driving – Parking and traffic are major considerations
Final Thoughts on a Perfect Chicago Weekend Trip
Chicago has so much to offer and we love to visit! You will have no trouble filling and enjoying your time for a short weekend getaway! Between a variety of accommodations, food, entertainment and transportation, visitors truly have so much to experience throughout the city of Chicago.
Have you tried any of these top suggestions in Chicago? Which locations from our list are you most excited to check out or what should we add to the list? Let us know in the comments!