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Wednesday, August 12, 2020

48 Hours of Fun On a Budget in Chicago


In this blog series I show you how easy it is to budget travel anywhere and I also give you a quick overview of a new city each time in a brief 48-hour itinerary.

While we're still in a makeshift quarantine, I've been thinking about trips we could take if we lived closer to some destinations. Chicago is in Phase 4 of reopening and is looking to entice tourists to come back. While I'm not willing to get on a plane, I know some of you are closer, or maybe you're interested in going in the future, which is my plan. 

Photo by Max Bender on Unsplash

I have planned a 2-day trip to The Windy City, assuming we're still in the middle of this pandemic. Some things are still closed. Some things are still not safe. Here's a perfectly reasonable way to spend 48 hours there with your mask and still have a great time. Here's how I would spend 2 days in the city right now:

As always, I assume you got in the night before and you've found a reasonably-priced place to stay. For this instance, I'm choosing your first day to be a Sunday, because that's when the street market is open (though it's also open Fridays), and because Saturday is a cheaper day to fly than Thursday, which is notoriously more expensive. This is also based on two people traveling.

Day1

Start your Sunday morning right with a trip to Maxwell Street Market where you can get up early browse some wares, buy some souvenirs if you like, and grab some of the best street food in the city. This is a perfect place to grab breakfast before your day out sightseeing. Estimate $20 for 2 to graze.


After breakfast, head to Skydeck Chicago at the Willis Tower for a beautiful view of the city. You can walk out to stand on the glass and, if you're brave enough, ride The Ledge, which tilts you out for a better view. This is best to make reservations ahead of time for, and if you look, you might find a promo code. $26pp, or included in the Chicago CityPASS*.


After seeing the sprawling skyline of your destination city, make sure you have your walking shoes on and visit the Chicago Riverwalk. Not only is it a wonderful walk, you can also bike, kayak, fish, or take a boat tour here. Take in the awesome free art along the way and stop to enjoy Art On theMART and memorials sprinkled throughout. Totally free to stroll.

Photo by Antonio Gabola on Unsplash


While strolling south, you'll find yourself at Millennium Park, home of the famous Bean, also known as Cloud Gate. Take your pictures, enjoy the park, which includes art exhibits, Lurie Garden (a 5-acre botanical park), as well as several play parks. 


Keep walking south until you get to Buckingham Fountain. This memorial fountain is one of the largest in the world and bordered on one side by a flower garden. Every 20 minutes (when in operation) it provides a water display that shoots 150 feet in the air. The fountain was open in 1927 and manually operated until the 1970s. It's the perfect setting for enjoying a delicious Chicago Dog from Buck's Four Star Grill. $25 for two if you include beer or hard cider and sides. If that's not for you, before entering Millennium Park, stop in at Bockwinkle's Deli and pick up something fresh to have whenever the mood strikes you.


Right around the corner is Shedd Aquarium. This conservation-forward aquarium has reopened with new safety precautions, including one-way walkways, touchtank unavailability, and no reentry to keep germs at as low as possible and prevent the spread of Covid as well as possible. You'll see endangered and thriving marine life here, with staff who are crazy about what they do and passionate about conservation and educating the public.  $39.95pp, included in CityPASS*, or free/discounted if you have a zoo/aquarium membership that participates in the Reciprocal Admissions Program (you must purchase entry tickets ahead of time)

By now you've probably walked off that hot dog and beer, but don't fear. Take an Uber or  walk back up the park to Navy Pier. It's open late, so you can walk along the water even after dark. There are plenty of places to shop, there's art, sculptures, gardens, and even live music. At the moment, all rides are shut down due to Covid, but that doesn't make it any less cool. 


Make a dining reservation somewhere a little upscale tonight. My choice would be outdoor dining at Riva Crabhouse. It's highly rated by diners and has a fabulous view of Lake Michigan. Choose from a variety of decadent seafood options, or steak dishes, to round off your first day out. Estimate $100 for two with entrees and shared appetizer or side.

Wander the pier a bit more or head back to your room to rest up for tomorrow. 


Day 2


Today is another day to wear your walking shoes and slather on some sunscreen. Hit up Dollop Coffee Co. to start your morning. Grab a steamy coffee drink and a pastry or a sandwich. Whatever fortifies you for your day. Estimate around $25 for two for a full meal. 


Two blocks west is a large greenspace which houses several cemeteries, including Graceland Cemetery, where many notable Chicago residents have been buried. You can take a self-guided tour (audio clips can be found on their website) of this historic cemetery opened in 1860 and see tombstones of people including Allan Pinkerton, Phillip Armour, and Victor Lawson. The cemetery is also an arboretum, so if you love nature, this is actually double cool, and has been called a hidden gem of the city.





A mile or so away finds you along the river at Lincoln Park Zoo. This free-to-the-public zoo might be small, but worth the visit. You'll have to reserve a free ticket ahead of time right now, but that's easily obtained online. There are more than 200 unique animal species and over 2,000 individual plants. This zoo has been in operation since 1868 and is one of the most established in the country. They work on conservation of animals in urban settings and boast a new eastern black rhinoceros calf, a cinerous vulture, and more animals you can't wait to see.

Head across the street to indulge in some great deep-dish Chicago pizza. I mean, if you don't, did you even visit? Hit up Ranalli's for dine-in (on the patio) or takeaway to eat in the park. You can also choose from salads, sandwiches, wings, and adult beverages. Estimate around $40 for two if splitting a large pizza - or a small pizza and sides - with booze.


Continue the outdoor love with a visit to Garfield Park & Conservatory. Just around 2 miles away, so you can easily walk or Uber or drive there. You will need to reserve your tickets in advance, but admission is free. This conservatory is one of the largest in the nation, with 2 acres inside greenhouses and an additional 10 acres outside. Through education, love of nature and discovery, the conservatory looks to bring people together and work on conservation of plants as a collective.

Now that you've taken in much of the free attractions, enjoy yet another one. Get a free one-hour tour with a Chicago Greeter. Book ahead for a tour of the city to learn more about the layout and history. Right now use of public transportation for this program is suspended, so you'll be doing a lot more walking. Though this is free, greeters work on tips, so I always allow $10-20 as a tip. 

Wow! I bet all the walking has made you both tired and hungry, even if you did eat that whole pizza. As you'll be close to Navy Pier, pop into Velvet Taco Gold Coast to grab an easy and yummy dinner that you can eat at the Ohio Street Beach (if it's open) or at Milton Lee Olive Park, or back in your room if you're tired of being out. If that's the case, you can also choose to have tacos delivered from one of their number of locations. Whether you're a vegetarian or a meat lover, Velvet Taco has something for you. The offer everything from Nashville hot tofu to a chicken and waffle brunch taco. Expect to spend around $5/taco, so I'd guess $35 for two people with sides and drinks.

Now it's time to head back and pack for your trip back home. For a social-distancing, mask-wearing trip, there are plenty of things in Chicago to do that are free or cheap. mix those in with more substantial attractions and you've got a nicely balanced trip that still comes out to a budget-friendly getaway. For two people, on the high end, you're looking at $397. If nothing else, you'll be getting fresh air and exercise in a new setting, where you can also sample local food.

Have you ever been to Chicago? What was your favorite thing to do, see, or eat there?

*Note: CityPASS is great, but several attractions on this are closed right now. Once they reopen, I'd consider buying and using to save money on the other attractions available besides the ones I've cited. This also includes an affiliate link.  

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