Gathering the gems worth your time…
Destination guide
Chicago
United States
Chicago is the home of the blues and the truth of jazz, the heart of comedy and the idea of the skyscraper. Here, the age of railroads found its center, and airplanes followed suit.
Introduction quoted from Wikivoyage, CC BY-SA
Sources gathered & checked 3 days ago
At a glance
- Best time to go
- April–June and August–October
- Getting around
- Taxi · Water taxi · Bicycle
- Vetted picks
- 30 places to see, do, eat, and stay
- Real coverage
- 5 vetted creator sources
AI insights
Computed from the Wikivoyage listings, transport section and YouTube view counts on this page
The most-viewed guide here is "4K Chicago Walking Vlog 2024 | Chicago’s Southside | Pill Hill Neighborhood | Chicago, Illinois" by Peaceful Explorations (2K views) — a solid first watch.
Peaceful Explorations is a creator from here, not a visiting channel — worth watching for what the guidebooks skip.
Getting around: by taxi, by water taxi, by bicycle and 2 more — the section below has the details straight from Wikivoyage.
15 of the places below list a real price from their own source — worth a scan before you budget the trip.
How these 30 picks are sourced
7 of 30 are named by a second, independent source — Lonely Planet, Eater and James Beard Foundation, and 3 others — and each card names its own. The remaining 23 rest on the reference article alone: we list them because Wikivoyage or Wikipedia documents them, not because anyone else vouched for them. We also watched 5 creator videos, 1 of them from local channels rather than visiting ones. 24 of the 30 descriptions are quoted word for word from Wikivoyage under CC BY-SA rather than written by us, as is the introduction above — each of those cards says so. What we add is the checking, the corroboration above, and the choice of which places are worth your time at all.What we can't promise is that it's still true. Venues close, hours and prices change, and we don't re-check them — a place here closed for good and sat on this page for a year before anyone noticed. The insights are AI-written from these sources and can be wrong too. Confirm anything you'd be sorry to be wrong about before you set out. Terms.
Watch first
Ranked by views and how well each landed with the people who watched it, judged against the other coverage of this place — plus a local creator where we found one.
4K Chicago Walking Vlog 2024 | Chicago’s Southside | Pill Hill Neighborhood | Chicago, Illinois
Peaceful Explorations · 2K viewsLocal
![TOP 10 things to do in CHICAGO [Travel Guide]](https://i.ytimg.com/vi/kFMHx6XwBk0/hqdefault.jpg)
TOP 10 things to do in CHICAGO [Travel Guide]
Hungry Passport · 856K views
CHICAGO TRAVEL GUIDE 🇺🇸⚾ Top 35 Things to Do, See, Eat, Drink & Experience in Chicago, Illinois, USA
Samuel and Audrey - Travel and Food Videos · 743K views
THE ULTIMATE CHICAGO TRAVEL GUIDE // Best Things to Do & Iconic Foods to Eat (4K Vlog)
Luis Gusto NYC · 185K views
🌆 15 BEST Things to do in Chicago 🌭 ULTIMATE Travel Guide
Go Places with Tati & Brennan · 93K views
Best time to go
Best window: April–June and August–October
January and February are the months to avoid — cold. The window below is when it is genuinely pleasant.
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
IdealGoodOkayOff-season
Rated from ten years of daily temperature and rainfall recorded at this destination, via Open-Meteo's ERA5 reanalysis. Hover a month for its real numbers.
Getting around
By taxi
Sears Tower — 36 years after it was built on US Route 66, North America's tallest building was redubbed the "Willis Tower" for a bunch of junk bond traders; even more surprising than the renaming was how little the owners got for it.
By water taxi
In the summer, water taxis are sometimes more convenient than the CTA, if you are traveling around the fringes of downtown. They are also a relatively cheap way to take in some offshore views. Two private companies operate water taxi services around the Loop.
By bicycle
Chicago has a bike path along the shores of Lake Michigan, making north-south travel very convenient as long as the weather is favorable by the lake.
By car
Avoid driving in downtown Chicago if at all possible. Traffic is awful, pedestrians are constantly wandering into the street out of turn, and garages in the Loop can cost as much as $40 per day (although services like SpotHero may have more reasonable…
By public transit
The best way to see Chicago is by public transit. It is efficient in terms of price, travel time, and safety. The Regional Transportation Authority (RTA) oversees the various public transit agencies in the Chicagoland area.
Transport notes from Wikivoyage, CC BY-SA 4.0.
What to see
Places are listed from Wikivoyage and our own sourced research. Worth it means a second, independent source names the place too; “3 sources agree” means three or more do — and each card names them, so you can check. Single source means the opposite, said plainly: the reference article lists it and nothing else we checked does.
Millennium Park
Worth itAlso recommended by Hungry Passport and 1 other
Stopped here on camera: Hungry Passport
On the E side of Michigan Ave btwn Randolph St and the Art Institute· Free
Long before it opened, Millennium Park had become notorious for delays and cost-overruns, missing its titular date by a wide margin.
Description quoted from Wikivoyage, CC BY-SA
Vetted sources
Art Institute of Chicago
Worth itAlso recommended by Lonely Planet
One of the world's great encyclopedic art museums, home to Grant Wood's American Gothic.
Vetted sources
Millennium Park / Cloud Gate
Worth itAlso recommended by Lonely Planet
Anish Kapoor's reflective 'Bean' sculpture anchors the park's public art.
Vetted sources
New Regal Theater
Single source1641 E 79th St
Built in 1927 as one of the South Side's most impressive movie palaces, done up in ornate Moorish Revival style, this theater was in operation well past the riots and up into the late…
Description quoted from Wikivoyage, CC BY-SA
Vetted sources
Frederick C. Robie House
Single source5757 S Woodlawn Ave· Moderate
This fabulously impractical house designed by Frank Lloyd Wright is one of the world's most famous examples of the Midwestern "Prairie School" of architecture, which aimed to create buildings with prominent horizontal lines evocative…
Description quoted from Wikivoyage, CC BY-SA
Vetted sources
Trump Tower
Single source401 N Wabash Ave
1362 ft. The Trump Hotel and luxury residential building is both the newest member of the Chicago skyline, completed at the beginning of 2009, and the tallest after the Sears Tower — indeed, it…
Description quoted from Wikivoyage, CC BY-SA
Vetted sources
Oak Woods Cemetery
Single source1035 E 67th St
Were it not for the somber atmosphere, Oak Woods would probably be one of Chicago's favorite parks as it is beautifully laid out and has four attractive elongated ponds.
Description quoted from Wikivoyage, CC BY-SA
Vetted sources
King Drive Gateway
Single sourceS Martin Luther King Jr Dr between 24th St & 35th St
A 1½-mile stretch of Martin Luther King Jr Dr full of plaques and monuments to the neighborhood's culture and history.
Description quoted from Wikivoyage, CC BY-SA
Vetted sources
What to do
Soldier Field
Single source1410 S Museum Campus Dr
Home of the NFL's Chicago Bears, and from 2020 home (again) to Chicago Fire FC of Major League Soccer.
Description quoted from Wikivoyage, CC BY-SA
Vetted sources
Rate Field
Single sourceSox-35th Red Line
Formerly known as New Comiskey Park and later as U.S.
Description quoted from Wikivoyage, CC BY-SA
Vetted sources
United Center
Single source20 Madison bus· Pricey
Home of the NBA Chicago Bulls and the NHL Chicago Blackhawks.
Description quoted from Wikivoyage, CC BY-SA
Vetted sources
Northwestern Wildcats
Single sourceRepresenting Northwestern University in seven men's and 10 women's sports in the Big Ten Conference.
Description quoted from Wikivoyage, CC BY-SA
Vetted sources
The Rink
Single source1122 E 87th St· Cheap
Ok, this place is cool. A roller rink oozing with South Side character and home to not a few serious skaters who flaunt their moves to smooth R&B and old school.
Description quoted from Wikivoyage, CC BY-SA
Vetted sources
Oak Street Beach
Single sourcebetween 500–1550 Lake Shore Dr
There is plenty of everybody doing everything at Oak Street Beach.
Description quoted from Wikivoyage, CC BY-SA
Vetted sources
What to eat
Alinea
Worth itAlso recommended by Michelin Guide and 1 other
Grant Achatz's avant-garde multi-course tasting menu that redefined American fine dining.
Vetted sources
Girl & the Goat
Worth itAlso recommended by James Beard Foundation and 1 other
Stephanie Izard's bold, shareable plates that opened in the West Loop in 2010.
Vetted sources
Pequod's Pizza
Worth itAlso recommended by Eater and 1 other
Caramelized-crust deep-dish pizza in Lincoln Park.
Vetted sources
Lou Malnati's
Worth itAlso recommended by Eater
Butter-crust deep-dish pizza from a family chain running since 1971.
Vetted sources
Chicago's Home of Chicken & Waffles
Single source3947 S Martin Luther King Jr Dr· Moderate
A great little place serving all sorts of different combinations of, as you might expect, chicken and waffles, as well as your standard soul food menu, expertly executed.
Description quoted from Wikivoyage, CC BY-SA
Vetted sources
Garrett Popcorn
Single source4 E Madison St· Cheap
Whether Garrett's shout-out-loud delicious popcorn is the cap to a good lunch or composes the entire meal is up to you and your conscience.
Description quoted from Wikivoyage, CC BY-SA
Vetted sources
The Violet Hour
Single sourceDamen Blue Line
Named after a line in T.S. Eliot's The Waste Land, The Violet Hour is hidden away — there's no sign, and no name on the door. Inside, though, is a marvelous, decadent, Alice-in-Wonderland plus…
Description quoted from Wikivoyage, CC BY-SA
Vetted sources
Coalfire Pizza
Single source65 Grand bus· Moderate
In the pizza wars between Chicago-style, Brooklyn, Naples, and gourmet-trendy, Chicago of course wins.
Description quoted from Wikivoyage, CC BY-SA
Vetted sources
Medici
Single source1327 E 57th St· Cheap
An Italian place very popular with the students, that can lay claim to above average baked goods, fine thin-crust pizza, Italian dishes, and a fun ambiance in their downstairs seating area (a separate door…
Description quoted from Wikivoyage, CC BY-SA
Vetted sources
Woodlawn Tap
Single source1172 E 55th St· Cheap
From the University perspective, this is the one and only real bar in Hyde Park (and accordingly, the only establishment that was saved from the University-driven "urban removal").
Description quoted from Wikivoyage, CC BY-SA
Vetted sources
Where to stay
The Palmer House
Single source17 E Monroe St· Expensive
With over 1,600 rooms and no shortage of luxuries, the Palmer House is one of Chicago's most memorable hotels.
Description quoted from Wikivoyage, CC BY-SA
Vetted sources
Congress Plaza Hotel
Single sourceLibrary CTA, Jackson Blue Line· Expensive
The Congress Hotel has seen visits from most U.S. presidents since it was built in 1893.
Description quoted from Wikivoyage, CC BY-SA
Vetted sources
The Drake
Single sourceChicago Red Line· Expensive
It was swallowed into the Hilton chain some years ago, but the Drake is still the definition of old Chicago elegance.
Description quoted from Wikivoyage, CC BY-SA
Vetted sources
The Robey Hotel
Single sourceDamen Blue Line· Expensive
Located in the renovated art-deco 1929 Northwest Tower, hotel features small but comfortable rooms immediately adjacent to the Damen Blue Line stop in the heart Wicker Park.
Description quoted from Wikivoyage, CC BY-SA
Vetted sources
Benedictine Bed & Breakfast
Single source3111 S Aberdeen St· Expensive
Cozy spacious rooms within an urban Benedictine monastery.
Description quoted from Wikivoyage, CC BY-SA
Vetted sources
Hostelling International Chicago
Single sourceLibrary CTA, Jackson Red Line, LaSalle Blue Line· Cheap
Right in the middle of the downtown college ruckus, HI Chicago is not far from Union and Ogilvie, but will take some navigating from either airport into Chicago.
Description quoted from Wikivoyage, CC BY-SA
Vetted sources
Build your day
Pick the places you want in Chicago, United States and we will put them on a map in an order that does not cross the city twice.
Where to next
More of United States we’ve vetted — nothing else is close by.
- New YorkThe country's densest concentration of world-class restaurants, museums, and Broadway theater.
- Grand CanyonA mile-deep gorge carved by the Colorado River, among the most dramatic landscapes on Earth.
- San FranciscoSteep hills, the Golden Gate Bridge, and a food scene anchored by Chinatown and the Ferry Building Marketplace.
- Los AngelesHollywood, beach towns from Venice to Malibu, and one of the country's most diverse food scenes.
- Las VegasCasino resorts, celebrity-chef restaurants, and nonstop entertainment on the Strip.
- YellowstoneThe world's first national park, with Old Faithful's geysers and free-roaming bison herds.
Travel content from Wikivoyage, CC BY-SA 4.0. Encyclopedic context from Wikipedia, CC BY-SA 4.0. Videos via the YouTube Data API.