Chicago Itinerary

For many couples and families, a long weekend in Chicago can be a quick and relaxing break. With an amazing skyline, friendly people, great music and wonderful food, spending three or four days in the Windy City is often a very cost-effective yet fun-filled weekend. Below is the trip plan we used but we always encourage families to adjust the lodging, activities and days to fit their preferences – but we hope this will provide you with a creative outline.

It is also important to vary your plans based upon whether you will be visiting in the Summer or Winter. You’ll have to decide between football and baseball; between outdoor parks and indoor museums; and boat tours or indoor activities based upon the weather.

For our trip, we were planning to visit in December (but we will add a few Summer variations as well to consider). We arrived early and if you have not been to Chicago before, we recommend against using a rental car. Parking is difficult and taxis are everywhere and very convenient. We had tickets to the Thursday Night NFL game between the Bears and Cowboys. But regardless of when you visit, you should try to schedule time for either a Cubs game or Bears game. Chicago is known for being a sports town and we had the added pleasure of talking to the grandfather in the seats next to us who was the epitome of the Chicago sports fan. We learned he has had his tickets for over thirty years and brings his boys with him to every game. You could not find more pleasant fans even when you are rooting for the opposing team.

Lodging is available for any price range – just be sure to try to stay somewhere on or near Michigan Avenue north of the river. This makes it much easier to walk to many of the most popular attractions. We chose the James Hotel which is a small, upscale and modern hotel since it was just the two of us on this trip.

Our first day we checked into the hotel and had reservations for lunch at the RL Restaurant. This is Ralph Lauren’s signature restaurant and store which is worth touring before you eat. They are known for the RL Burger (prime Angus on challah bread which is one of our favorites) and their Corned Beef and Swiss with thousand island dressing and rye bread. The restaurant is surrounded by wood walls on all sides and has high back chairs so it has an English lounge feel to it.

Afterwards, we walked out to spend some time on Michigan Avenue. Many families will want to visit the Skydeck at Willis Tower. However, there are often long lines and you can pay anywhere from $15 to $25 per person to go up and stand in a small glass box on the outside of the building. It makes for a good photo but has a very touristy feel. A local friend gave us a great tip to skip the Skydeck and go to the Hancock Tower instead up to the Signature Lounge on the 96th floor. It does not cost anything (other than a glass of wine). There are no lines and you still get the 360 degree views of the city and lake while enjoying a drink.

Afterwards, we grabbed a cab over to Gibson’s for another drink in the lounge where there is usually a piano player and some great people watching – and then another cab (yes, they are that easy to get) to the football game. We only stayed through the third quarter and then headed to Au Cheval in what our friend’s called the Oprah District. Apparently, this area was home to Harpo Studios which led to a rebirth of the area and is now filled with restaurants. Harpo left the area but the resurgence remained. Au Cheval is a communal style restaurant where we tried bone marrow (not a fan – tastes like buttery fat) and a few sandwiches and burgers. However, nearby is also the very popular Girl and the Goat but whatever you choose, it is worth spending some time in the area for dinner.

The next morning we had breakfast at Yolk’s, a Chicago chain who later opened a location in Dallas as well. For the morning, you can head over to Millennium Park which will take a good hour or more to see. During the Summer you can find the Buckingham Fountain running (as seen in the opening credits of the show, Married with Children), as well as the Cloud Gate sculpture (often referred to as The Bean), large outdoor modern sculptures, gardens and venues. If you are traveling in the Summer, be sure to check to see if there are any events happening during your visit. Just south of the park is the Art Institute of Chicago. Even if you are not a fan of art, this is worth a few hours. The museum is on par with the finest in the world and you’ll be amazed at just how many paintings you recognize.

After a long morning of walking, you can head over to The Gage across the street. It is quite popular but worth the wait for a table. We cannot recommend enough trying the Scottish Egg (hard-boiled egg wrapped in sausage and then coated in bread crumbs and fried) and the House Poutine Fries (fries covered in cheese curds and gravy – trust us, it’s worth trying). Your traveling so why not try something new. You might be surprised.

If you are traveling during the Summer, we have heard nothing but positive reviews of the Architectural Boat Tours along the coast and river. It was a bit too cold for us but TripAdvisor lists a number of top options and we feel is something we would do with kids when we return for a Summer trip – as well as a Cubs game at Wrigley Field.

After lunch, there is some time to rest or shop along Michigan Avenue before dinner. You are in Chicago so pizza and blues music is a must. We won’t bother getting into which is the best pizza. Everyone has a favorite from Lou Malnati’s to Pizzeria Uno to Bartoli’s and so on. However, if you asked us, our favorite is Ranalli’s in Lincoln Park. They make a double-decker pizza with two pizzas cooked separately and then placed on top of each other so the crust is still crispy. It is served like a lasagna which you eat with a knife and fork. The front half of the restaurant is all brick and you often find Chicago policeman and firefighters eating at the tables next to you adding to the appeal. We also chose this area as it was a short walk to B.L.U.E.S. for some live music.

Chicago has a variety of blues venues. They range from those which are very popular with visitors (Green Mile) to some which are very popular with musicians (Buddy Guy’s Legends) and some which are a bit off the beaten path (B.L.U.E.S.) We chose the latter due to its proximity to our dinner and to try something a bit more adventurous. It is very, very small and you will be sharing tables with people dancing the entire time. So if you want something a bit more roomy and less of a dive atmosphere, you can’t go wrong with Buddy Guy’s either. But B.L.U.E.S. does provide a very authentic music experience.

Late night is great at Clark and State streets. You can visit the famous Mother Hubbard’s Sports Pub for some drinks and then over to O’Callaghan’s late into the evening. Remember bars are open in Chicago until 4 a.m. for the late night crowds. And it is very clear the locals start their evenings later than in other cities.

The next morning you can have breakfast at The Lobby in the Peninsula to cap off your weekend – and then a few hours exploring Michigan Avenue again shopping and buying some gifts for the kids. It’s then back to the airport for the flight home after a weekend of sightseeing, art, pizza, blues and sports.

DAY 1 – chicago – hancock tower, gibson’s, bears or cubs game

Fly to Chicago early
Views from the Hancock Tower Signature Lounge
Drinks around the piano at Gibson’s
Soldier Field Football game (Winter) or Cubs Game Wrigley Park (Summer)

Eat: RL Restaurant ($$) – Lunch (RL Burger, Corned Beef and Swiss); Au Cheval ($$) or Girl and the Goat ($$)
Stay: The James Hotel – ($$) or any other hotel of your choosing

DAY 2 – chicago – MILLENNIUM park, art institute, pizza, blues, nightlife

Millennium Park – Sculptures, Fountains, Concerts
Art Institute of Chicago
Blues (B.L.U.E.S., Buddy Guy’s Legends or Green Mile)
Nightlife (Mother Hubbard’s, O’Callaghan’s or any of the bars on Clark and State Street)

Eat: The Gage ($) – Lunch (Scottish Eggs, Poutine Fries); Ranalli’s (Double Decker Pizza) or any other pizza – Dinner ($)
Stay: The James Hotel – ($$) or any other hotel of your choosing

DAY 3 – chicago – shopping, home

Shopping on Michigan Avenue

Eat: The Lobby at the Peninsula ($$) – Breakfast
Stay: Your own bed.

And for more details on other large cities see our full itinerary for San Francisco/Napa or Los Angeles/SoCal or destination notes for San Francisco and Los Angeles.