2 Amazing Days in Chicago: Hotel With a View, Where to Eat, and Things To Do

If you’ve only got 2 days to enjoy the beautiful city of Chicago, you’ve come to the right place. My hometown is visited and loved by many tourists. It has been voted the best city in the U.S. for several years past by Condé Nast Traveler.

2 Days in Chicago

Chicago is huge and has lots to offer, so planning well is vital. This includes staying in the ideal location with a fantastic view, booking activities, and reserving your spot at the best restaurants. Luckily, with my experience, I have plenty of tips (and linked posts) for your weekend Chicago trip.

Hotel With a View–Holiday Inn Chicago Dwtn Wolf Point

First things first, where you stay for only 2 days in Chicago is important. And boy, do I have the perfect place for you!

The Holiday Inn Chicago Dwtn – Wolf Point, an IHG® hotel, is located in the heart of Chicago and offers gorgeous river and city views. It has been recently renovated and shares space with the voco Chicago hotel.

I just had an incredible weekend stay in one of their corner suites, and I loved waking up to the buzzing of the city below and the postcard views in front of me.

Our room had wall-to-wall windows with views of the river, the bridges, and even the famous (my favorite) John Hancock building. If you’re looking for a hotel with a view, this is it.

The Holiday Inn Chicago Dwtn Wolf Point sits in the River North neighborhood, one of the best areas in the city. It’s next door to the Merchandise Mart and across the street from the Chicago River.

The location is especially ideal for first-time visitors. You can walk to many great attractions and are close to the L train, boat tours, and water taxis. Plus, you can take in the city views from every direction (day or night) from the comfort of your room.

The Merchandise Mart has “Art on theMart” happening nightly in the summer, where they project digital art on the building’s facade. As mentioned, you’ll find this next door to the hotel.

It was fun to see the boat tours going down the river, kayakers trying to avoid the boats, and the L train zipping by between the buildings—all from our hotel window. Trust me; you won’t tire of this classic Chicago scene.

We enjoyed their room service with one of the prettiest charcuterie boards I’ve ever seen. The hotel also has a newly renovated restaurant/bar, Waterview, that opens across the 15th floor with panoramic skyline views.

So even if you don’t book a skyline room, you can still enjoy the view from the bar. The drinks were delicious (try their old fashioned and lemon drop martini), and the servers and bartenders were so kind.

Besides all the perks I’ve already shared, the Holiday Inn Chicago Dwtn Wolf Point is a special place for us. My husband and I had our wedding here in 2011. It was a beautiful event and one of the best days of our lives.

Many people raved about the view and the food for years after! So if you’re looking for an event space, check out their website for more info.

We snuck in to see the ballroom during our stay, which flooded us with wonderful memories.

You can find even more amenities at Holiday Inn Chicago Dwtn Wolf Point: a big indoor pool, kids under 12 stay and eat for free, and you can book and collect IHG One Rewards with your visit. But just with the views and service alone, you won’t regret your stay!

IHG Rewards

Speaking of IHG One Rewards, I’ve collected these rewards for years in my travels. Being a free Club member allows you to earn points for reward nights at many IHG hotels (free stays), access to member rates and offers, no blackout dates, and late checkout (2 pm). You can join for free here.

I’ve also had the IHG credit card (on top of rewards) for years and have enjoyed one free “Anniversary” night yearly. Thanks to this free night, we’ve stayed at some gorgeous hotels around the world.

It helps to bring hotel costs down when traveling or to enjoy a local getaway at a snazzy hotel.

View from a free hotel stay in Paris:

InterContinental Paris Le Grand view

Rooftop view from a free hotel stay in London:

Where to Eat

Anyway, back to Chicago! During our weekend stay, we loved our stop at the new Blue Bottle Coffee along the Chicago River, across from the hotel.

The cafe sits in the prettiest corner, and the coffee is delicious. I think as a visitor, it’ll be a treat to sit outside with your latte and enjoy the city.

Below is the scenic walkway from the hotel to the cafe.

And if you want to beat the heat (or cold) the inside of the cafe also has good views.

For dinner, we made reservations at one of our favorite steakhouses, Bavette’s Bar & Boeuf. Order the petite filet mignon; you won’t regret your choice. We finished the night with great drinks at the hotel bar.

If you’re looking for more ideas on where to eat in Chicago, I have several posts on all the local favorites.

Things To Do in Chicago

My weekend Chicago trip was all about the views! I bought tickets to see the Goo Goo Dolls at Huntington Bank Pavilion on Northerly Island and fell in love with the venue.

If you’re visiting the city during a warmer season and want to do something unique, check out what concerts are playing at this venue. Even the walk to and from Northerly Island hits a lot of Chicago landmarks.

Below is the Museum Campus on the walk back from the concert.

Besides the concert, dinner, drinks, and Art on theMart, I spent most of my 2 days relaxing with the views at the hotel. But you can do so much more in the city close to the Riverwalk (or beyond).

If you’re looking for more photo opportunities, you can find that post here: Chicago Photo Locations.

If you’re planning the holidays and want a winter/Christmas guide for Chicago, read this: Things to do in Chicago in December.

Sometimes tours can help you experience the highlights of a city or even the local treasures—especially if you only have a few days to explore. I’m linking a few fun and best-rated tours. Click the links for all the details.

I hope this post gave you some good ideas on what to do with your 2 days in Chicago. Make sure you start with a hotel with a view!


Thank you to Holiday Inn Chicago Dwtn Wolf Point for hosting us. As always, all opinions are my own. This site contains affiliate links. I may receive a small commission for purchases made through these links at no extra cost to you.


  • Reply Jen August 13, 2022 at 12:17 pm

    This is great, planning a 2 day trip right now and looking for some different things to do having been there a few times (plus, gonna be a super budget trip) Saving this for later!

    • Reply Lily August 13, 2022 at 9:20 pm

      Glad it was helpful 🙂

  • Reply The Elegant Wanderer August 13, 2022 at 12:00 pm

    Very useful post as I’m planning to visit Chicago! I see some great recommendations here, thank you for sharing 🙂

    • Reply Lily August 13, 2022 at 9:20 pm

      Thanks for reading!

  • Reply Nikki August 13, 2022 at 11:56 am

    Wow, what a great guide! I’m heading to Chicago for a weekend in October. I don’t have a hotel booked yet so will definitely look at availability based on your recommendations! Thanks!

    • Reply Lily August 13, 2022 at 9:20 pm

      October is my favorite month in the city! You’re in for a treat!

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