A Long Weekend in Chicago: River Views, Museums, and Room to Return

Brian and I went to Chicago in July 2023 for a long weekend, and it gave us exactly what we hoped a big-city getaway would: an easy flight into O'Hare, an exciting downtown skyline, plenty of things to do, and more good food choices than we could possibly work through. The weather was beautiful for most of the trip, with one memorable rainstorm on our final day.

Like several of our other city trips, we decided a more expensive downtown hotel was worth it. We could walk to many of our plans, return to the hotel when we needed a break, and avoid turning every sight into a commute. That choice made a short visit feel much more relaxed. We took a taxi from O'Hare; the CTA Blue Line is also a direct, practical option for travelers comfortable using the train.

We did not try to conquer Chicago. Instead, we chose a river tour, a few museums and walks that matched our interests, and a little time to see how the city felt. We still missed plenty, but that is part of the reason we talk about going back.

CityPASS or à la carte? Our short-weekend answer

We considered a Chicago CityPASS before the trip, but we ultimately booked our attractions one at a time. We did not think we would have enough time to use a larger pass well, and I would rather spend a little more intentionally than feel pressure to squeeze in an attraction just because it is already paid for.

I remember the pass options we considered in 2023 differently from what is offered now, so I would not use our choice as proof of a current inclusion. Today, CityPASS lists a three-attraction Chicago C3 option and a five-attraction CityPASS option, and the Shoreline Sightseeing Architecture River Tour appears among the current choices. It can be a good value when the exact attractions and reservation times already fit your plan; for a short visit like ours, compare the total for the experiences you truly intend to do before buying.

Our first priority: a 75-minute architecture river cruise

We booked a 75-minute architecture river tour for $59 per person in 2023, and it was the experience I would most quickly repeat. Seeing Chicago from the river makes the downtown skyline feel less like a set of separate buildings and more like one story about the city. It was a wonderful first overview before we began walking around on our own.

The guide connected familiar landmarks with the people, engineering, and eras behind them. A river route can vary, but these tours typically travel the main branches of the Chicago River and point out buildings such as the Wrigley Building, Tribune Tower, the Merchandise Mart, Marina City, and Willis Tower, along with the older and newer structures around them. I especially enjoyed watching the river open out among the towers and seeing how dramatically the view changed from one block to the next.

Book ahead if a river cruise is a priority, especially for a summer weekend. I would also choose a departure with a little breathing room around it. You do not want to be sprinting to a boat dock after a flight or leaving the boat already late for a timed museum entry.

Navy Pier: beautiful lake views, very real crowds

We also walked Navy Pier. The Lake Michigan views were lovely, and I am glad we saw this well-known part of the waterfront, but it was very crowded during our visit. That is not a reason to avoid it; it is simply a reason to set expectations. I would treat it as a scenic walk and choose one or two specific things to do rather than expecting a quiet escape.

Navy Pier has free general entry, with restaurants, shops, boat tours, the Centennial Wheel, seasonal rides and programming, public art, and family options such as the Chicago Children's Museum. It can be a natural choice for a family, a lakefront view, or a boat departure, and it offers a very different perspective from the river. In summer, however, leave time for crowds and check the current calendar rather than assuming every attraction or event will be running when you arrive.

The American Writers Museum was made for this English teacher

Because I am a retired English teacher and we both love a literary connection, the American Writers Museum was an obvious stop. It was enjoyable, well curated, and exactly the sort of museum that makes a city trip feel personal rather than generic. The exhibits invited us to move beyond a list of famous names and think about the many forms American writing can take: novels, poems, speeches, journalism, song lyrics, children's books, and the daily work of writers and readers.

We especially appreciated the interactive approach. The museum's permanent galleries include a timeline of American writing, the Word Waterfall, the Mind of a Writer gallery, a Chicago-focused gallery, a children's space, and reader-centered displays. The Chicago material was a fitting addition to a city already so connected to journalists, poets, novelists, and people who have used writing to question the world around them. Temporary exhibitions and programs change, so I would check what is on before a future visit.

Day two: the Museum of Science and Industry at our own pace

The next day, we went to the Museum of Science and Industry, now called the Griffin Museum of Science and Industry. It is a huge, hands-on museum and could easily be a five-hour visit if you let it. We were ready to move on after a few hours, which was right for our weekend, but that did not mean we had run out of things to see.

This museum is especially strong for families with children, curious teens, multigenerational groups, and adults who enjoy interactive science more than a quick walk past display cases. Its signature experiences include the U-505 submarine exhibit, which tells the story of a German submarine captured during World War II; the Coal Mine, a guided descent into mining history; Science Storms, with large-scale demonstrations of natural phenomena; transportation displays; and substantial aviation and space artifacts. Some tours, theatre experiences, and special exhibitions require separate or timed admission, so check that before deciding what a day should include.

The rotating exhibitions are part of what lets repeat visitors have a different experience. During our 2023 visit, Pompeii: The Exhibition was one of the special exhibitions, while the permanent galleries gave us plenty of choices even without trying to see every room. My advice is to decide whether your group wants the major add-on experience, a special exhibition, or a broad sampler of the permanent museum. Trying to do all three in one short visit can turn an interesting place into an exhausting one.

An afternoon of gangsters, ghosts, and the Loop

That afternoon, we took the Chicago Gangsters and Ghosts walking tour. It gave us a different way to see the Loop, using stories of the old vice district, speakeasies, bootlegging, crime scenes, and supposedly haunted locations to make the streets feel more layered. We enjoyed the historical storytelling and the excuse to keep walking after a museum morning.

The current version of this walking tour is about two hours and 1.5 miles, beginning near the Royal Sonesta Hotel at Wacker and Wabash. Its listed stops include the Congress Hotel, Death Alley, and the Palmer House, with the exact route and stories subject to change. It is marketed as history-based rather than a theatrical scare experience, which was a good fit for us. Wear comfortable shoes and think of it as an atmospheric city-history walk, not a substitute for a museum-level account of Chicago's complex past.

Magnificent Mile window-shopping and a rainstorm Portillo's order

Yes, Michigan Avenue's famous shopping district is the Magnificent Mile, and we spent some time walking it. We window-shopped, enjoyed the energy and architecture, and did not buy anything. That was perfectly fine. On a trip like this, I enjoy having an unstructured walk between ticketed experiences; it lets a city feel less like an itinerary and more like a place.

We found food options plentiful and generally very good throughout the weekend. On the rainy final day, we used DoorDash and ordered Portillo's because we had heard about it. My honest review: the Italian beef sandwich arrived soggy and was only so-so for us. The chocolate cake shake sounded odd but was genuinely good. I am glad we tried a Chicago institution, but I would not let one delivered sandwich become anyone's entire food plan for the city.

We had hoped to find a Broadway-style show for the weekend, but nothing playing interested us enough to book. That is now part of our return-trip conversation: choose a production we really want to see, then add more of the museums, neighborhoods, food, and lakefront time we did not reach the first time around.

What I would do differently on a return

I would still stay downtown, still take the architecture cruise, and still keep the itinerary selective. I would give the river and lakefront more time, pair the weekend with a show that matters to us, and make room for a few sights we skipped instead of trying to add them all at once.

Chicago is not a city I would try to finish in a weekend. Our trip worked because we accepted that from the beginning. We came home with a good first impression, several experiences we really enjoyed, a few candid food opinions, and a clear reason to go back.