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Maybe it’ll be your first visit to Chicago or you’re looking for a different experience on your annual visit, either way, Chicago is amazing, and you will have a wonderful time. You may not even notice that there’s still a pandemic, besides the use of face masks everywhere. Everything is starting to feel like it’s getting back to normal. Be sure to visit the city website before you travel to understand any current travel restrictions.
At the time of this post, there is an Emergency Travel Order:
Based on data as of 5/17/2021
In response to the changing dynamics of COVID-19 transmission across the United States, and to support Chicago’s efforts to contain the spread of COVID-19, the City is issuing a Travel Order applicable to anyone coming into the City of Chicago from designated states with a significant degree of community-wide spread of COVID-19. Anyone traveling from a state on the Orange list is directed to obtain a negative COVID-19 test result no more than 72 hours prior to arrival in Chicago or quarantine for a 10-day period (or the duration of their time in Chicago, whichever is shorter). The Order is subject to the limited exemptions outlined in the ‘Exemptions tab’.
In my experience of traveling to Chicago, yes, I was aware of the order and I was fully vaccinated at the time of travel. No, no one ever asked me for my vaccination record so I’m not sure when or how that is enforced. As always, follow the rules and be prepared for anything though because I believe we all experience different things. One person’s truth does not equal another’s.
Just a Reminder…
You’ll find a lot of links to various resources on this site, some of these links are affiliate links that pay me a commission at no extra cost to you. If you make a purchase through these companies, this supports the photos and tips that are provided to inspire you in your own travels.
Late Night Arrivals
One thing that I miss the most is how this city never sleeps! If you find yourself on a late-night flight into Chicago, you do not need to worry because there is always somewhere to eat in the middle of the night. Having late night access to food spoils you and does not prepare you for the places where everything is closed by 8pm. I’m still not used to that.
Arriving in Chicago at midnight? Depending on what part of the city you’re headed will determine what you can get. If you just want a McDonald’s or Wendy’s, there’s usually a 24 hour one somewhere. You will find a few places near the airport but here’s some native favorites for late night iconic eats:
Lawrence Fish & Shrimp
2120 S Canal St, Chicago, IL 60616
I’ve never been a fan of most fish so my favorite thing here is the Wing Zings. Wing Zings are deep fried wings with a little kick, I don’t consider it to be spicy, but my spice palate has a deeper range than most people. If you are a vegetarian, well, this might not be the stop for you. I knew going home meant I’d probably nibble on a little meat here and there, it’s so hard in meat town! I was so happy to see that they had online ordering now, the order was ready quickly, AND they’ve grown to several new locations!
100 W Ontario St, Chicago, IL 60654
You must get an Italian beef – dipped, preferably with hot peppers and try the chocolate cake. If you are vegetarian – I love gravy bread and this location makes the best, toasted, and married to the gravy, they become one. Trust me, Florida Portillo’s does not make it like this, I don’t think they trust that when I say I want it wet; I mean dunked and baptized like sins are being washed away. Sadly, they are only open until midnight.
The Original Maxwell Street
601 S Sacramento Blvd, Chicago, IL 60612
This McDonald’s (23 S Clark St, Chicago, IL 60603) used to be called the Rock & Roll McDonald’s and was open 24 hours, it was a staple in Chicago memories of late-night fun. In 2017, they changed it to a regular McDonalds that closes by 10PM.
White Castle – 2140 S Wabash Ave, Chicago, IL 60616
There are plenty of 24-hour ones throughout the Chicago area.
Why all the junk food? What else did you think would be open in the middle of the night? A quick google map search will also pop up some late-night diners and dives too. You never know what you will find, but you won’t have to go to bed hungry.
Parking & Public Transportation
Chicago has one of the easiest systems to understand, it is a well-organized grid. Madison Street divides the city North and South. State street divides East and West. CTA makes it easy to get around with buses, trains, and direct airport transit to downtown.
You can also take a Chicago Water Taxi on the river.
Driving is easy but aggressive. This is not the place to be a timid driver. The hardest thing though, may be parking. A downtown hotel may have valet only parking at $60 – 75 per night. Most people are shocked by the price. It’s okay though, because if you don’t mind some planning tricks and a short walk, you can still stay downtown and pay as little as $15 per night. Using these apps to plan your parking, you can find and reserve spots early, change the time on a reservation if you need more flexibility, and save big while living your downtown dream adventure.
The only thing more shocking than the valet parking is the tax on a car rental from the airport. One more way to save on both is a one-way rental for the day if you don’t want to take public transportation. Avis, Budget, and Hertz have downtown locations and a one way special that can be picked up and dropped off within 12 hours starting at $9.99. Trust me, this is the best! I’ve used it in New Orleans and Chicago. Priceless money savings hack.
This also works great if you fly into O’hare and are leaving from Midway (or vice-versa). For instance, the lowest quote for a minivan for the week was over $800. Instead, I picked up a full-size at O’hare on a late night arrival, dropped off downtown the next morning for $30. While dropping it off, picked up a minivan to return to Midway days later. That rental was only $350 after taxes. Saved more than half the price.
Get Outside in Chicago
I’m not going to spend a lot of time talking about it because you should know, there’s this big lake (Lake Michigan) and along it is plenty of beach. North Ave Beach is one of the most popular. If you’re going there, I say, live your best life and make a reservation at the Shore Club Chicago Oasis. $50 will get you a daybed from 11AM – 4PM or 4PM to 9PM (up to 10 guests).
- Small cabana $150
- Large cabana $200
- Get Rose Bottle Service starting at $250 or 6 packs that range from $30 non-alcoholic to $60 for spiked seltzers.
Photo Below by Amit Thakral on Pexels
Grab your friends and go for that total Basic Beach Package for $750
6 White Claws
6 High Noon
6 Red Bulls
6 Michelob UltraShore Club Chicago Oasis
I’m a south sider so I’d probably go to 31st Beach or Margaret T. Burroughs Beach, very laid back, plenty of parking, and you can settle in nicely for a day of picnics and sun. This beach has a long history and while the park district only focuses on the positive newer history, I cannot leave out what happened at this beach more than 100 years ago during the Red Summer of 1919. This is always referred to as “race riots” but I prefer “race massacre”. The beach used to be segregated and those imaginary lines and feelings of entitlement and superiority led to the massacre of 38 people with hundreds injured and burned out of their homes. I like to keep the mood light, but we cannot ignore the past, it must be embraced if we ever want to be better from it. Take a moment to gasp at the view of Chicago’s skyline from this beach and look forward to its future.
The beach is open from 6 am to 11 pm, but swimming is only permitted when lifeguards are on duty, from 11 am to 7 pm daily.
- No smoking.
- No alcohol.
- No dogs on the beach.
- ADA-accessible playground
- “green roof” picnic area
- public fishing dock
- community room
- harbor store
- 1,000 floating slips
Assuming that you want to stay close to downtown and do most of your exploring on foot, here’s what you can see and do without a car, or with a quick share ride, taxi, or public transportation:
Great for restaurants and wandering. You can also admire ArtontheMart (video projections on the world’s largest commercial building) nightly from 9pm to 9:30pm from here.
You can work your way from Cloud Gate and the Lurie Garden through the Cancer Survivor’s Garden at Maggie Daley Park to the Buckingham Fountain and South Rose Garden.
Up on the rooftops
Chicago’s rooftop scene is jam packed with views, drinks, and good eats all around. Read my post about 3 that I visited recently. Yes, you will want to make reservations early.
Want a speakeasy experience?
Be on the lookout for this secret bar to open back up! Watershed Bar. Enter through Pops for Champagne and take the stairs down. Until that one opens, I would definitely put the Drifter on the bucket list. Vintage, historic, real speakeasy from the days of Prohibition. You may have to wait to get in. $4-6 cover charge, no reservations. You’ll find it in the basement of the Green Door Tavern. The menu changes daily with over 100 cocktails presented on Tarot cards. I’m not even sure I’m cool enough for this place. 676-8 N Orleans St, Chicago, IL 60654
My favorite 2 Chicago cruises:Chicago Architecture Foundation Center River Cruise on Chicago’s First Lady – honestly, the Architecture Foundation has the best tours of Chicago. You can’t go wrong with them, you will be entertained and fascinated. You can’t help but picture the city evolving right before your eyes.
Seadog Cruises at Navy Pier – Extreme Thrill Ride is the one to go with. High speeds and full 360° spins, best ride I ever had.
Can’t decide between all of the museums? You can get a Chicago Pass and see a few, just go the free ones, or use your local museum membership for reciprocal rights at participating members. NARM will get you into 10 museums in the Chicago area including DuSable Museum of African American History and the Chicago History Museum. Visit the Field Museum, the Museum of Science and Industry, Peggy Notebaert Nature Museum, and the Adler Planetarium with an ASTC membership.
Chicago CityPass from $100+ per pass or join your local museum, family membership with reciprocal benefits could cost you as little as $60 depending on your museum and family size. Joining your local museum supports the arts in your community, gives you discounts and special invites, and can be used when you travel to do and see more for less.
Public art and street art
No room in the budget or time for the Art Insitute? Picasso, Calder, and Chagall are right on the street.
- Agora by Magdalena Abakanowicz – 1135 S Michigan Ave, Chicago, IL 60605
- CloudGate (the Bean) by Anish Karpoor – 201 E. Randolph St., between Michigan Ave. & Columbus Ave.
- Crown Fountain by Jaume Plensa – Millennium Park, 201 E. Randolph St., between Michigan Avenue and Columbus Avenue.
- The bright red Flamingo by Alexander Calder – Federal Plaza, 50 W. Adams St.
- The Four Seasons (of Chicago) Mosaic by Marc Chagall – Chase Tower Plaza, 10 S. Dearborn St.
- Monument with Standing Beast by Jean Dubuffet – 100 W Randolph St, Chicago, IL 60601
- Muddy Waters Mural by Eduardo Kobra – 17 N. State St.
- The Picasso – 50 W. Washington St.
- Wabash Arts Corridor (a living urban canvas) – 635 S. Wabash Ave.
While you’re in the area, stop by Harold’s (612 S Wabash Ave) and try the catfish, the chicken is good, but the catfish is a bright shining star. Get the mild sauce. On it. Yes, on it. Thank me later.
Want more? – Head over to the Chicago Loop Alliance.
Theatre and Performances
Another one of my favorite things to do in Chicago, from seeing Wicked at Broadway in Chicago to Phantom of the Opera or Carmen at the Lyric Opera House. Look for upcoming shows like Hansel and Gretel in the Park. Most of my ways to save on tickets have gone out the window with the pandemic, they just can’t afford to discount them right now. But when things return, hopefully you’ll be able to find discounts again with Hot Tix and Goldstar.
Summer Fun & Festivals 2021
Sundays on State Street – free block party on Sundays beginning July 11.
My beloved SummerDance is expected to return this August – September 2021. Learn all the classic dances and maybe some you don’t know like Chicago Step. Bring a partner or come alone. Dress up or dress down. Enjoy the people watching if you’re not a dancer, beginners are encouraged to join in, it’s for everyone!
Dine out on Broadway or Sheffield in Lakeview Fridays – Sundays. See participating restaurant list. Streets will be closed during that time and public transportation will be re-routed.
The Candlelight Concert series with live musicians.
For a FREE guided walk, reserve with Chicago Greeter.
Enjoy Chicago from home with Your Night Out at Home from Chicago Park District. Watch everything from jazz to dance and theater performances.
Pride in the Park starts June 26, 2021.
Grant Park Music Festival starts July 2, 2021.
The Lyrical Lemonade Summer Smash – 3 Day Hip Hop Music Festival in August with 75 artists and 3 stages.
You could easily gorge yourself on a different pizza each night and it will be different every single time. Ask any Chicagoan and they will all give you a different answer for best pizza and best Italian beef in the city. I, personally, have never met pizza in Chicago that I didn’t like except for one but it is so wildly popular that I dare not say it aloud. Actually, 2 come to mind but no one agrees with me on either. Let’s just say the toppings are very THICK. My personal favorites are Foxes which you will have to travel to the far south side for and Giordano’s which you can get downtown.
When you’re done gorging on fried comfort food, you’ll want to try some new flavors and different cuisines like these:
- Girl & The Goat – 809 W Randolph St, Chicago, IL 60607
I remember when this one first started making headlines and we hurried to try it. Glad to see it’s still there and keeping mouths happy. It’s so good, even Michelin thinks so. Vegan and Vegetarian friendly with good eats like chickpea fritters (sumac yogurt . green chutney . sev spice crunch | 15) or wood grilled broccoli (smoked bleu cheese . spiced crispies | 15). Check the menu.
- Ramen-San – 59 W Hubbard St #2, Chicago, IL 60654
Ramen and sake bombs, dine-in or order and pick up.
- The Purple Pig – 444 Michigan Ave, Chicago, IL 60611
Another Chicago favorite with vegetarian and vegan friendly options. The salt roasted beets might make you rethink whether you like beets or not.
- Star of Siam – 11 E Illinois St #1, Chicago, IL 60611
Love the tempura here!
- Corner Bakery – 360 N Michigan Ave ENTRANCE ON, E Wacker Dr, Chicago, IL 60601
Lots of locations and good breakfast with a lovely caramel macchiato that made me happy every single morning.
- Potbelly Sandwich Shop – 190 N State St, Chicago, IL 60601
Great salads and sandwiches, and they have hot peppers like I like them.
- Carson’s Ribs – 465 E Illinois St, Chicago, IL 60611
Another old time favorite.
Try the exotic truffles at the Chocolate Temple Boutique or find it in O’hare airport.
- Boka Restaurant *Michelin* – 1729 N Halsted St, Chicago, IL 60614
- Hugo’s Frog Bar & Fish House *Michelin* – 1021 Atlas Peak Road, Chicago, IL 60611
- The Publican *Michelin* – 837 W Fulton Market, Chicago, IL 60607
There are so many places and styles of food to eat that Chicago is one of the few places I truly feel comfortable eating almost anything. Take one of my favorites or find something new, you’ll be eating good either way.
Want to help support Black-owned businesses while eating well? Take a look at Black People Eats for featured restaurants. You’ll find places like Batter & Berries – 2748 N Lincoln Ave, Chicago, IL 60614 and Fruve Xpress Juicery– 1130 S Wabash Ave, Chicago, IL 60605, for your ACAI Bowl fix.
Should you be looking for a Chicago Cannabis Guide try this list of the Best Dispensaries in Chicago.
There’s so much more to wander in Chicago. Have fun!