The Ultimate Chicago Weekend Getaway Itinerary

Whether you are coming into the city from out of town or are a local staycation-er, this Chicago weekend getaway itinerary will satisfy your big-city cravings, recharge you and have you playing tourist in the United States’s third biggest city.

Before we dive into the getaway itinerary, though, we have to be honest with ourselves.

Is Chicago A Good Weekend Getaway?

Yes, Chicago is a fantastic weekend getaway option for those who love touring big cities, relaxing my the beach or hotel spa, shopping and/or watching sunset from a rooftop bar.

However, if you’re looking for a getaway that is more low-key without big-city hustle and bustle, I instead recommend Door County, Wisconsin, or Washington Island, Wisconsin, both of which are only a few hours north of Chicago.

Where Can I Get Away In Chicago?

The best places to get away in Chicago are Lincoln Park (North Avenue Beach, zoo and botanical gardens), Millennium Park (nature, public concerts and activities, fountains and “The Bean”), local spas, and hotel rooftop pools and bars.

Like I said, Chicago is an amazing weekend getaway destination. You will have the opportunity to visit all of these Chicago getaway spots and more with the following itinerary.

Now, let’s get to it. Here’s how to spend a weekend in Chicago.

Chicago Weekend Getaway Day 1

1. Morning: Coffee, Millennium Park And The Shedd Aquarium

Plan to start your first day early.

By 8:00 a.m. at the latest, go out to grab some coffee and breakfast. If you’re a loyal Starbucks drinker but want a local experience, visit the Chicago Starbucks Reserve Roastery. If you’re traveling on a budget and bank with Capital One, head to the nearest Capital One Cafe (all cardholders get 50% off drinks).

By the way, I have an entire downloadable ebook that teaches my exact method for traveling on a budget. It’s called the Budget Travel Bible — you can find out more about it here.

Then, walk to Millennium Park. Here, you’ll get to see iconic Chicago attractions like Cloud Gate (AKA “The Bean”), Crown Fountain, Art Institute Of Chicago, Buckingham Fountain, Jay Pritzker Pavilion and more.

As you pass through the park, make your way toward the legendary Shedd Aquarium.

Here, you’ll have the unforgettable opportunity to see endangered beluga whales, dolphins, massive sharks, stingray, as well as plenty of tropical and local fish.

Or, if aquariums aren’t your thing, visit the Art Institute Of Chicago or the Field Museum Of Natural History, which are respectively located within and adjacent to Millennium Park.

2. Afternoon: Architecture River Cruise

After a morning of parks and museums, grab a non-pizza lunch (you’ll be having pizza for dinner). My readers recommend the Nutella Cafe for a fun non-pizza meal.

Then, head toward your Chicago Architecture River Cruise dock. Not only do you get to learn about the city’s epic architecture on the tour, but you also get to spend 60-90 minutes cruising on the Chicago River. Talk about a perfect Chicago weekend getaway activity.

We booked our cruise tour with Wendella Boats, and although the best seats were taken before we arrived, we stood in the very front of the boat and had great views. I recommend that you get to your dock at least 45 minutes before the beginning of the tour to get good seats.

3. Evening: Deep Dish Pizza And The Chicago River Walk

When in Chicago, you need to eat deep dish pizza at least once.

In my humble opinion, Giordano’s has the best deep dish pizza in Chicago, hands-down. I’ve tried all of the other major deep dish pizza places in the city (Lou Malnati’s, Gino’s East and Uno’s), and Giordano’s truly cannot be beat.

Because you’ll be stuffed to the brim with deep dish, the last Chicago weekend getaway itinerary item for day one is to help your food digest on the Chicago Riverwalk.

The Chicago Riverwalk, a pedestrian walkway along the Chicago River, is very popular among both locals and tourists. Between the beautiful cityscape and river views, there’s no doubt that the riverwalk is one of the most recharging things to do in Chicago.

Chicago Weekend Getaway Day 2

1. Morning: Coffee, Lincoln Park

To start off the second day of your Chicago weekend getaway, grab coffee and breakfast around the same time as the day prior.

Then, make your way to Lincoln Park, arguably the best park in the entire city.

At Lincoln Park, you can sunbathe on the ocean-like sandy North Avenue Beach, enjoy one of the best Chicago skyline views, journey through the Lincoln Park Zoo, explore the Lincoln Park botanical gardens or walk on the park’s paved, tree-covered trails.

Oh, and all of these activities are completely free. You just have to pay for parking!

2. Afternoon: Chicago SkyDeck And/Or 360 Chicago

After a relaxing park morning (and perhaps a picnic lunch), go back to the downtown area for even more incredible Chicago views at the Chicago SkyDeck and/or 360 Chicago.

The Chicago SkyDeck and 360 Chicago are both sky-high city observation decks. They each have their own perks (which you can read about here), so you can choose which exhilarating view suits you best — or experience both.

Whichever attraction you chose, purchase tickets ahead of time. And, don’t forget your camera!

3. Evening: Dinner And Sunset At The LH Rooftop Bar

Finally, to end your Chicago weekend getaway, indulge in sunset dinner and drinks at the LH Ocean Prime the LH Rooftop Bar.

Perfectly overlooking the Chicago River, the LondonHouse Hotel offers a weatherproof indoor bar on level 21 and a bougie roofless bar on level 22.

If you want a table, you need to book reservations well in advance. But, if you can’t get a reservation, you can still watch sunset from the bar’s standing room space. There are tons of other restaurants near the LondonHouse too.

Bonus Chicago Weekend Getaway Things To Do

Of course, this Chicago weekend getaway itinerary accounts for two full days, but I know that some weekends look different from others.

Perhaps, you arrived in Chicago on Friday evening, and now you have a little extra time to explore. Or, maybe the weather isn’t great, and you want to stay indoors.

Here are some bonus things to do in Chicago to ensure you waste no time:

• Shop on Michigan Avenue.
• Bring out your inner child on Navy Pier.
• Watch a Cubs game at Wrigley Field.
• Splurge on a spa day.

You can read about these Chicago activities and more here.

Can You See Chicago In A Weekend?

Yes, you can absolutely see Chicago in a weekend. While there are endless things to do in Chicago, this Chicago getaway itinerary will help you maximize your weekend in Chicago and see everything you want in a short period of time.

As someone who was raised just a few hours away from Chicago, I’ve been to Chicago a handful of times. I can assure you, all the activities listed in this itinerary are the most iconic things to do in Chicago. You won’t miss a thing with this itinerary!

Regardless, if you have any questions at all, don’t hesitate to leave a reply below or send me a message on Instagram. I’m more than happy to help you.

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