Now that you’re convinced there are many sights to see and restaurants to eat at in Chicago, let’s talk about the logistics. Read on for tips on how to get around the city and what you should think about when planning your trip.
The most important thing to think about when visiting Chicago is the weather. Anytime except winter would be your best bet. Chicago’s winter snow is lovely but it could turn into Snowpoloypse, which can cause flight delays and activity closures. Many of Chicago’s activities are outside or at least, you will need to walk outside to get to them. It’s doable – I went in January my first trip – but it’s much more enjoyable in the summer. In July, the temperatures got up to the high 80s.
Fly into the O’Hare (ORD) or Midway (MDW) airport. Both are international and have trains going straight into downtown: Blue line from O’Hare or Orange line from Midway.
Public Transportation: the “L” (elevated train)
The L is very easy to use to get around Chicago. There are lines directly from both airports into downtown and stops are a walkable distance downtown. Use Google Maps to lead you to the closest stops and the right train route and you’re set! A 3-day unlimited ride pass is $20.
Private Transportation: Taxis, Uber or Lyft
All of these private transportation methods are available in Chicago and are easy to find in the downtown area.
Alternative Way to See the City: Rent a Bike
You’ll find racks of blue Divvy bikes for rent around downtown.
Check the events calendar
In the summertime, there are plenty of activities going on in Chicago. These may be great options for you or a good time to avoid visiting Chicago because of higher costs and crowds. Check out the city’s events calendar for free outside festivals and other events.
Best Views of the City
There are many places to see scenic views of Chicago. As I mentioned in the top things to do in Chicago post, Signature Lounge or 360 Chicago at the John Hancock Center and Skydeck at the Willis Tower are good choices up high. You’ll find a skyline view on the ground from the museum district by the Shedd Aquarium or Adler Planetarium. Inside the Art Institute of Chicago will get you some interesting views too.
Go Chicago Card
Planning on visiting multiple Chicago attractions? The Go Chicago Card gives you access to 26 attractions at a discounted price. Prices differ from how many days you’ll be sightseeing: 1, 2, 3 or 5 days, and prices range from $85-$175 for adults and $60-$119 for children. There are also different passes and pricing if you want to visit 5 or less attractions.
Similar to the Go Chicago Card, the Chicago CityPASS gives you entry to 5 attractions for a discounted price. It allows you to skip ticket lines and gives you 9 days to use your book.
Check out my recommendations of top things to do in Chicago for ideas.
When looking for a place to stay, I recommend staying close to downtown and/or by an L stop.
We stayed at the Kinzie Hotel for the weekend. It was a great location – close to the Riverwalk, a few blocks from the L, and walking distance to many restaurants. While the hotel felt small because of the entryway and lobby, the room was comfortable, colorful, and sleek. We enjoyed the perks of complimentary Wi-Fi, fruit-infused water in the afternoons, and breakfast snacks (drinks, cereal, donuts, yogurt, pastries, fruit) in the morning. We didn’t get the chance to check out their daily reception but there is one available. They do have pet-friendly rooms and a fitness center. Though we did spend most of our time exploring Chicago, the hotel was a lovely place to re-energize and get a good night of sleep!
Budgeting a trip to Chicago is very easy because of free activities and cheap eats. In splitting the check for all our meals, no meal was over $30. From $3 hot dogs at Portillo’s to $14 entree plates at Avec, Chicago’s eats are affordable with planning.
Check out my eating and drinking in Chicago post for recommended restaurants, drinks and snacks.
What tips would you add for a great trip to Chicago?