I remember stepping off the train at Union Station last summer, that first blast of wind hitting my face – yep, the Windy City lives up to its name. I spent five days trying to cram everything in, and let me tell you, some things stood out way more than others. Forget those generic "top 10" lists. After getting lost near Wrigleyville, eating way too much deep dish, and almost freezing on that lakefront, I've put together the real essential must do things in Chicago based on what actually delivers.
Millennium Park and Cloud Gate (The Bean)
You simply can't claim you've done Chicago without seeing the Bean. It's cliché, sure, but there's a reason everyone flocks here. That mirrored surface reflecting the skyline? Pure magic, especially at dawn when the crowds are thin. Getting that perfect selfie takes patience though – prepare for photo-bombers.
Practical Stuff You Need:
- Address: 201 E Randolph St, Chicago, IL 60602
- Hours: Park is open 6 AM - 11 PM daily. The Bean area is accessible anytime.
- Cost: Totally free! (Major win)
- Getting There: Easiest via CTA 'L' trains - Red, Green, Orange, Blue, Purple, Brown, or Pink lines to Washington/Wabash or Monroe stations. Buses #3, 4, 6, 20, 56, 60, 124, 151 all stop close.
- Time Needed: Plan 45-90 minutes depending on photo ops and exploring the rest of Millennium Park (Lurie Garden, Pritzker Pavilion).
Is it touristy? Absolutely. But skipping it feels like going to Paris and ignoring the Eiffel Tower. One of the undeniable must-dos in Chicago.
Art Institute of Chicago
Even if you're not an "art person," this place floors you. Seeing Grant Wood's American Gothic up close gave me chills. Their Impressionist collection competes with the Met in NYC. Last time I went, I got completely lost in the Thorne Miniature Rooms – tiny, perfect historical interiors. Mesmerizing.
Can't-Miss Masterpieces
- Georges Seurat's "A Sunday on La Grande Jatte": The pointillism is insane up close.
- Edward Hopper's "Nighthawks": That lonely diner vibe hits different.
- Modern Wing Architecture: The building itself is art.
Now here's my gripe: it's HUGE. Trying to see everything in one visit is a recipe for sore feet and museum burnout. Pick a wing or two.
Visitor Essentials
| Info Type | Details |
|---|---|
| Address | 111 S Michigan Ave, Chicago, IL 60603 |
| Hours | Thu-Mon: 11 AM - 5 PM (Closed Tue/Wed) |
| Tickets | Adults: $32 | IL Residents: $25 | Teens (14-17)/Students: $25 | Kids 13 & under: Free (Pro Tip: Check for free admission days - usually Thursdays 5-8 PM for IL residents!) |
| Transport | Adams/Wabash or Monroe 'L' stations (Green, Orange, Brown, Purple, Pink lines). Bus #3, 4, 6, 7, 126, 147, 151. |
| Time Budget | Minimum 3 hours. Easily 5+ for art lovers. |
Booking tickets online saves you queue time. Trust me, the line can snake around the block on weekends. This museum is a cornerstone of Chicago must-see activities.
Chicago Architecture River Cruise
Hands down the best way to understand Chicago's skyline. I was skeptical – a boat tour? Really? But the docents (often from the Architecture Foundation) are incredibly knowledgeable. You learn why those Wrigley Building terraces exist, the drama behind Marina City, and how the city rebuilt after the fire.
Not all tours are equal though. I took a cheaper one once and regretted it – muffled audio, crowded deck. Spring for the official Chicago Architecture Foundation Center Cruise.
Cruise Operator Comparison
| Company | Duration | Price Range (Adult) | Key Feature | Boarding Location |
|---|---|---|---|---|
| Chicago Architecture Foundation Center Cruise | 90 min | $47 - $54 | Expert docents, highly educational | Michigan Ave & Wacker Dr (SE corner) |
| Wendella (Architecture Tour) | 75 min | $41 - $47 | Good coverage, open-air & covered decks | 400 N Michigan Ave (DuSable Bridge) |
| Shoreline Sightseeing (Architecture Tour) | 75 min | $42 - $48 | Multiple departure points | Navy Pier or Michigan Ave (Tribune Tower) |
| Speedboat Tours (e.g., Seadog) | 30-75 min | $30 - $50+ | Thrilling ride, less detailed commentary | Navy Pier |
Essential Tips: Book ahead, especially sunset tours. Bring layers – it gets windy on the river even on warm days. A daytime cruise offers better visibility for architectural details, sunset offers killer photos. This consistently ranks as a top must do thing in Chicago for good reason.
Devouring Deep Dish Pizza
Let's settle the debate: Chicago pizza isn't just deep dish. There's stuffed (thicker, more cheese), and there's thin crust tavern-style (cracker-thin, cut into squares). BUT, for the quintessential experience, deep dish is mandatory. It's a meal, not a snack. One slice will fill you up.
My personal take? Lou Malnati's butter crust is legendary, but Gino's East has that iconic cornmeal crust texture. Giordano's stuffed pizza feels like a cheese avalanche – delicious, but maybe skip dinner afterward.
Chicago Deep Dish Showdown
| Spot | Signature Style | Must-Try Pie | Average Pie Price | Key Location | Vibe |
|---|---|---|---|---|---|
| Lou Malnati's | Buttercrust (thin, flaky) | The "Malnati Chicago Classic" (sausage) | $25 - $35 (med) | Multiple, including River North & Lincoln Park | Classic, family-friendly, efficient |
| Giordano's | Stuffed (thick layer cheese) | Special (sausage, peppers, mushrooms) | $28 - $40 (med) | Multiple, including Magnificent Mile & South Loop | Touristy spots, lively, can be loud |
| Gino's East | Cornmeal Crust (distinct texture) | Meat & More Meat Deep Dish | $26 - $38 (med) | Multiple, including River North | Graffiti-covered walls, boisterous |
| Pequod's | Caramelized Cheese Crust Edge | Sausage Deep Dish | $24 - $36 (med) | 2207 N Clybourn Ave (Lincoln Park) | Neighborhood pub feel, cult favorite |
Important: Deep dish takes time! Don't go starving. Expect a 45-60 minute wait for your pizza to bake fresh. Order an appetizer (their salads are surprisingly good). Tavern-style is great too (try Pat's or Vito & Nick's), but deep dish is a non-negotiable must-do thing in Chicago for your taste buds.
Navy Pier Views and Attractions
Navy Pier divides locals. Some find it overly touristy, and yeah, the crowds and chain restaurants can be a turn-off. But walking to the very end and looking back at that skyline? Worth it. The Centennial Wheel gives incredible panoramic views without the Skydeck crowds or price. Go late afternoon to catch sunset over the lake.
Navy Pier Essentials
- Address: 600 E Grand Ave, Chicago, IL 60611
- Hours: Shops & Restaurants: Vary (often 10 AM - 8 PM), Attractions like Centennial Wheel: Typically 11 AM - 9 PM (Summer), shorter hours off-season. Pier grounds are open early/later.
- Cost: Free entry to the pier. Centennial Wheel: ~$15 adults. Other attractions (rides, mini-golf) priced separately. Combo passes available.
- Getting There: Bus #29, 65, 66, or 124. Walkable from Michigan Ave (about 15-20 mins). Water taxis (Shoreline, Wendella) run from Michigan Ave or Riverwalk.
- Time Budget: 2-4 hours depending on rides/meals.
My Advice: Skip the mediocre chain food. Grab a Chicago-style hot dog from one of the carts near the entrance instead. Visit on a weekday for shorter lines. While touristy, the views and energy make it a classic must do in Chicago, especially with kids.
Conquering the Skydeck at Willis Tower
Stepping onto The Ledge is a legit adrenaline rush. Looking straight down 103 floors through glass? Your knees might wobble. The view is undeniably spectacular on a clear day, seeing all the way to Indiana or Michigan. But man, the queues can be soul-crushing. I waited 90 minutes once – brutal.
Skydeck Survival Guide
- Address: 233 S Wacker Dr, Chicago, IL 60606 (Enter on Franklin St)
- Hours: Typically 9 AM - 10 PM daily (check website off-season).
- Tickets: General Admission: $35-$50+ (Dynamic pricing - higher on weekends/sunset). Buy timed tickets ONLINE in advance! Skip-the-line options cost more.
- Getting There: Quincy 'L' station (Brown, Orange, Purple, Pink lines). Bus #1, 7, 28, 126, 134, 151, 156.
- Time Budget: Minimum 2 hours (including security, elevator, viewing). Add 1+ hours for peak time queues.
Alternatives Worth Considering:
- 360 CHICAGO (Hancock Building): Same height, equally stunning views. Often shorter lines. Their TILT experience is wild (you lean out over the city!). Costs similar to Skydeck.
- Signature Lounge (Hancock): Buy a drink (pricey, $15+ cocktails), enjoy the same view as the observation deck below... for cheaper! Go before sunset for a seat.
Is the Skydeck a must do Chicago experience? For the thrill and bragging rights, yes. Just plan strategically to avoid wasting half your day.
Chicago Neighborhoods Worth Exploring
Downtown is great, but Chicago's soul lives in its neighborhoods. Wandering beyond the Loop reveals the real city.
- Wicker Park/Bucktown (Blue Line Damen stop): Hipster central. Amazing thrift stores, indie coffee shops (like Wormhole), street art, diverse food (try Big Star Tacos). Feels vibrant and creative.
- Lincoln Park (Brown/Purple Line Armitage or Fullerton): Beautiful tree-lined streets, the free zoo (Lincoln Park Zoo!), fantastic boutiques on Armitage Ave. Feels affluent and charming. The zoo is genuinely impressive and free – great for families.
- Pilsen (Pink Line 18th St stop): Heart of Chicago's Mexican community. Incredible murals everywhere (walk down 16th St), authentic taquerias (Carnitas Uruapan is iconic), National Museum of Mexican Art (free!). Full of color and culture.
- Andersonville (Red Line Berwyn stop): Historic Swedish roots, now LGBTQ+ friendly. Cozy cafes (Kopi Cafe), unique gift shops, great brunch spots (M. Henry). Feels welcoming and village-like.
Getting lost in at least one neighborhood is a must-do thing in Chicago if you want to move beyond the postcard.
Chicago Sports Madness
Chicagoans bleed their team colors. Catching a game is electrifying, even if you're not a die-hard fan. The energy is contagious.
- Wrigley Field (Cubs): Historic, ivy-covered walls. Pure baseball nostalgia. Tickets: Vary wildly ($20 bleachers to $200+ behind home). Take Red Line to Addison. Bleacher seats are rowdy fun.
- Guaranteed Rate Field (White Sox): South Side pride. Often cheaper tickets, more relaxed vibe. Take Red Line to Sox-35th. Famous for their fireworks.
- United Center (Bulls/Blackhawks): Jordan's house (statue outside!). Intense basketball/hockey atmosphere. Take Blue Line to UIC-Halsted. Tickets pricey, especially for big games.
- Soldier Field (Bears): Lakefront location, iconic columns. Brutal in winter, but classic NFL grit. Bus #130 or walk from Roosevelt 'L' (Red/Green/Orange lines). Tickets: Very expensive.
Even just bar-hopping near Wrigleyville during a Cubs game is an experience. Feeling that city-wide buzz is definitely among the top must do things in Chicago during season.
Must Do Things in Chicago: Budget vs Splurge Options
Chicago can be pricey, but it doesn't have to break the bank. Here's how to experience the essentials at different price points:
| Experience | Budget Friendly Must-Do | Splurge Worthy Must-Do |
|---|---|---|
| Iconic Views | Lincoln Park Zoo Views (Free!), Adler Planetarium Lawn Skyline View (Free Grounds Access) | Skydeck Chicago or 360 CHICAGO TILT ($35-$55) |
| Architecture | Self-guided Loop walking tour using Chicago Architecture Center app (Free), Pedway exploration | Official CAF Architecture River Cruise ($50+) |
| Lakefront Experience | Rent a Divvy bike ($15+/hour) & ride Lakefront Trail, Relax at Oak Street Beach | Lake Michigan sailing charter ($75-$150+) |
| Food Experience | Chicago-Style Hot Dog (Under $5 at Portillo's/Al's), Garrett Popcorn snack ($8-$12 bag) | Signature deep dish pizza dinner ($25-$40 pie) |
| Cultural Experience | Lincoln Park Zoo (Free!), Museum of Mexican Art (Free!), Millennium Park concerts (Free in summer) | Art Institute of Chicago ($32+), Steppenwolf Theatre tickets ($60+) |
Chicago Must-Do FAQ: Answering Your Real Questions
What are the absolute must do things in Chicago for a weekend trip?
Focus on the core: Millennium Park/Bean (free), Art Institute (half day), deep dish pizza dinner, an architecture cruise (90 mins), and one skyline view (Skydeck or 360 CHICAGO/Signature Lounge). Add a neighborhood stroll (Wicker Park or Lincoln Park). Ambitious, but doable!
What unique must-do things in Chicago often get missed?
Locals know these gems: Garfield Park Conservatory (free, stunning indoor gardens), walking the 606 elevated trail (like NYC's High Line), catching blues music at Kingston Mines (open late!), or the free Lincoln Park Conservatory. The Cultural Center downtown (free) has a breathtaking Tiffany dome.
Is Navy Pier worth it? It gets mixed reviews...
Honestly? It depends. If you hate crowds, skip the shops/rides and just walk to the end for the skyline view (free) or ride the Centennial Wheel ($15). It's worth it for the vista, especially at sunset, but prioritize other sites if time is tight. It's iconic, but not universally beloved.
What's the best deep dish pizza in Chicago?
This starts arguments! Pequod's has a fiercely loyal following for its caramelized crust edge. Lou Malnati's wins for classic butter crust. Giordano's is famous for stuffed (cheese overload). Gino's East has the distinct cornmeal crust. You really can't go *wrong* with the big names. Try one, then argue about it later!
What should I absolutely avoid in Chicago?
Renting a car downtown is expensive and stressful. Don't try to drive everywhere. Avoid Navy Pier restaurants (mediocre chains; eat elsewhere). Don't limit yourself to just downtown – explore a neighborhood! Don't underestimate walking distances – use the excellent CTA 'L' trains. Don't forget layers – weather changes fast. Finally, don't skip the lakefront – it's Chicago's crown jewel.
Is the Chicago CityPASS worth it for hitting the must-dos?
If you definitely plan to visit Skydeck/360 CHICAGO, the Field Museum OR Shedd Aquarium, AND the Art Institute OR Museum of Science & Industry, then yes, the CityPASS saves significant money (~40%). Calculate your planned entries first. If you prefer neighborhoods or free activities, skip it.
What's the best way to get around for doing all these Chicago must-sees?
The CTA (Chicago Transit Authority) is your friend. Buy a reusable Ventra card ($5, plus load value) for unlimited train ('L') and bus rides. Uber/Lyft are plentiful. Walking is great downtown/lakefront. Avoid driving! Trains connect major sites (Loop), neighborhoods, and airports.
When is the best time to tackle all these Chicago must do activities?
Best Weather (Shoulder Seasons): Late May-June & September-October. Pleasant temps, fewer crowds than summer.
Peak Crowds/Festivals (High Prices): July-August (Lollapalooza, Taste of Chicago), December (Christkindlmarket).
Budget/Cold Tolerance: November-March (cheaper, festive holidays, but COLD and potentially snowy). Spring (April-May) can be rainy but blooms are pretty.
Look, Chicago's got layers. You could spend a month here and barely scratch the surface. But ticking off these core must do things in Chicago gives you the iconic views, the deep flavors, the architectural wonder, and a real feel for the city's energy. Don't stress about doing everything. Grab a hot dog, look up at those skyscrapers, feel that lake breeze, and take it all in. That's the Chicago must-do, above all else.
Comment