Chicago is perfect for a fun-filled weekend getaway or longer 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 with skyscraper views, the windy city makes for a great weekend 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 pleasurable, 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! 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!
Table of contents
Where to Stay in Chicago
Ensuring you’re in a comfortable place will ensure you’re able to rest at the end of your busy tourist day, which is why your choice of accommodation is so important. Before booking a hotel, motel or guesthouse, checking the amenities and services that are offered allows you to guarantee your unique needs will be met.
The Langham Chicago
Star Rating: 5
Price Per Night Starting At: $475
Pendry Chicago
Star Rating: 4.7
Price Per Night Starting At: $165
Peninsula Chicago
Star Rating: 5
Price Per Night Starting At: $450
Viceroy Chicago
Star Rating: 4.5
Price Per Night Starting At: $203
Other Great Hotel Contenders: The Blackstone, Four Seasons Hotel Chicago, and Londonhouse Chicago Hilton Curio Collection
Booking.com
What 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 Go-City All inclusive Pass that includes over 25 different experiences in the windy city!
Built 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!
- Millennium Park & Cloud Gate(The bean) – It is a gem with 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.
- Wrigley Field – A classic must-do! 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!
- Skydeck Chicago – Willis Tower – Beautiful views from the 103rd floor observation 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 – Located in the Streeterville area of Chicago on Lake Michigan with many activities and fun things to do.
- Buckingham Fountain – Beautiful fountain in Grant Park at 301 S. Columbus Drive usually open May-October
- The Magnificent Mile – Posh area located on the North end this area includes luxe shopping, famous buildings like the Hancock. and many restaurants
Chicago Natural Attractions
- 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
- 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.
- World Music Festival Chicago (September) The World Music Festival Chicago is a city-wide, multi-venue celebration of international music held annually in September. The event features artists from around the globe, offering attendees a chance to explore diverse musical styles and cultures through live performances and workshops.
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
- Chicago Riverwalk – Public space on the south bank of the Chicago River with many bars, restaurants, and shopping.
- 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
Whether you are a foodie traveler or just want to try Chicago cuisine, you’re going to sit down and eat something, as it is an essential part of life, 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 hot dog!
Alinea [Contemporary American]
Atmosphere: Fine Dining and Luxurious
1723 N Halsted St
Definitely a foodie favorite restaurant and a must-try!
Giant – [Gastropub]
Atmosphere: Minimal, funky and Classic
3209 W Armitage Ave
Craft cocktails here are also amazing!
Kasama – [Filipino]
Atmosphere: Modern Fine Dining
1001 N Winchester Ave
Serves pastries, food, and wine!
Lula Café – [American]
Atmosphere: Funky and casual farm to table restaurant
2537 N Kedzie Blvd
Be sure to try their great brunch too!
Mi Tocaya Antojería [Mexican]
Atmosphere: Vibrant and Casual
2800 W Logan Blvd
Great small plates and cocktails!
Monteverde – [Italian]
Atmosphere: Inviting and Airy
1020 W Madison St
Fresh pasta and a great wine list!
Pequod’s Pizza – [Pizzeria]
Atmosphere: Quaint and Casual
2207 N Clybourn Ave
A must try for the deep-dish Chicago-style pizza!
Smoque BBQ – [Barbecue]
Atmosphere: Neighborhood Gathering Spot
3800 N Pulaski Rd
Community tables and amazing bbq!
Superdawg Drive-In – [Hot Dog Stand]
Atmosphere: Old School Nostalgia
6363 N Milwaukee Ave
Car Hops still deliver food at this classic drive in hot dog stand!
Other Great Foodie Contenders: Carnitas Uruapan, Daisies, and J.P. Graziano Grocery.
How to get Around Chicago
Transportation is an important aspect of any vacation that ought to be considered in terms your arrival and your inner city travels as well.
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: 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 accommodations 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!
Thank you for the tips on where to go and the restaurants. I will be in Chicago again this summer and will try to visit a few of these. George’s Deep Dish pizza on N Clark has been my favorite on every trip so far.
Hi there, thanks for the deep dish recommendation. We will definitely check it out next time.