

Photos: Chicago by Jesus Toledo, Pexels License; Philadelphia by Trev W. Adams, Pexels License.
Chicago or Philadelphia?
Our verdict in twelve categories, each scored against the same fixed benchmark cities, and the climate month by month, so you can choose for your trip.
Choose Chicago for
- nightlife
- food and drink
- beaches
Chicago is the better choice if you want a big city at full strength for a week. It eats better at every level, from tavern-cut pizza to the tasting menus of the West Loop. It stays out later, with bars pouring until 4am, and it has the stronger stage, from the Symphony to storefront theatre and blues clubs. Its architecture and lakefront museums make it the easier sell with children too. Its weak spots are a long, hard winter and a flat hinterland with few outings worth the effort.
Choose Philadelphia for
- day trips
- prices
- nature and the outdoors
Philadelphia suits travellers who care about American history and like to range beyond one city. Independence Hall, Society Hill and the Barnes give it a deep few days on their own, and the Northeast rail corridor puts New York, Baltimore and Washington within easy reach for a day out. It also costs a little less, and its winters are milder. You give up some depth in food, nightlife and shopping.
Scoreboard
Twelve categories on one fixed scale from 0 to 100. The shaded stretch is the gap between the two.
Your match
Pick a travel style or drag the sliders, and both match scores follow your weighting.
Wins on nightlife and food and drink with your weighting.
Wins on day trips and prices with your weighting.
What matters to you?
Category by category
What the scores mean for a trip.
Beaches & swimming
Chicago has something Philadelphia simply does not: sandy beaches inside the city. You can swim at Oak Street Beach in the shadow of the Gold Coast towers or play volleyball at North Avenue, then be back at a museum within the hour. The fresh lake water is only warm enough in high summer, though, and it can turn cold overnight.
Philadelphia's swimming means a drive of well over an hour to the Jersey Shore, to Ocean City, Wildwood or Cape May. The Atlantic sand is wider and the sea is real surf, but it takes a whole day, and summer weekend traffic comes with it.
Food & drink
Both cities have a sandwich culture they are proud of, Italian beef and the dressed hot dog in Chicago, the cheesesteak and roast pork with broccoli rabe in Philadelphia. Above that level, Chicago goes much further. Randolph Street's restaurant row and the tasting-menu kitchens give it fine dining Philadelphia does not try to match, and the immigrant neighbourhoods, from Pilsen to Argyle Street, add real range.
Philadelphia's strengths are more intimate. Reading Terminal Market and the Italian Market are better places to graze than anything Chicago has, and the bring-your-own-wine dining rooms of East Passyunk and Fishtown make for relaxed, good-value dinners.
Culture & sights
Both are serious museum cities with a famous Impressionist collection, the Art Institute in Chicago and the Barnes in Philadelphia. Where they part is in what you look at between museums. Chicago is a city to look up in: the Loop's early skyscrapers, Mies van der Rohe's glass towers and the river cruise past them, plus Frank Lloyd Wright in Hyde Park and Oak Park. It edges ahead for the sheer scale of its sights.
Philadelphia offers what Chicago admits it lacks, history from before the 19th century. Independence Hall, the Liberty Bell, Elfreth's Alley and the Georgian rowhouses of Society Hill make it the place to walk through the founding of the country. Eastern State Penitentiary and the Mütter Museum add some odder detours.
Nightlife
Chicago is the stronger night out by some distance. Bars there stay open until 4am, against Philadelphia's 2am last call, and there is a real club scene in River North that draws on the city's place in the birth of house music. Wicker Park and Logan Square cover cocktails and dives, and Northalsted is a large gay district.
Philadelphia does a good evening in a pub rather than a big night. Fishtown's warehouse bars, Rittenhouse cocktails and the long-established Gayborhood are enjoyable, and the student crowd keeps weekends lively, but dancing until late is hard to find.
Nature & outdoors
Neither city has dramatic scenery, and they are broadly level here. What you get differs in kind. Chicago's outdoors is the open lakefront: a path of about 29km along the shore, best by bike, with Indiana Dunes and the canyons of Starved Rock reachable for a day.
Philadelphia's green space is more enclosed and wooded. The Wissahickon gorge feels like real forest inside the city limits, the Schuylkill River Trail leads out past Boathouse Row towards Valley Forge, and the Poconos and the Pine Barrens give it a little more variety further out.
Day trips
This is Philadelphia's biggest advantage. Sitting on the Northeast rail corridor, it can send you to New York, Baltimore or Washington by train for a full day out. Lancaster County's Amish country, Princeton, Gettysburg, Longwood Gardens and Valley Forge give a choice few American cities can match.
Chicago is surrounded by prairie, and its outings are pleasant at best. Milwaukee by train and the Wright houses of Oak Park are the easy ones. Lake Geneva and the Michigan harbour towns need a car and a fair amount of driving.
Good for families
Both cities rely on their museums with children, but Chicago has more of the big crowd-pleasers. The Museum of Science and Industry's coal mine and U-boat, the cluster of Field Museum, Shedd Aquarium and planetarium, the free Lincoln Park Zoo, Navy Pier and summer beaches add up to a fuller week.
Philadelphia answers with the Franklin Institute's giant heart, the Please Touch Museum for under-eights and the country's oldest zoo. Old City's costumed guides also make history easy for older children to follow. Its compact centre is easier on small legs, but some streets and stations are grubby.
Getting around
Chicago's L does the heavy lifting. The elevated trains run straight from both airports into the Loop, and once there, Millennium Park, the Art Institute and the Museum Campus are an easy walk apart. The catch is crossing between outer neighbourhoods, which often means a slow bus along one of the long avenues.
Philadelphia relies more on your feet. Center City is a compact rectangle between the two rivers, and most visitors walk everything from Old City to the Parkway without needing a car. SEPTA's subway and trolleys are rougher and less useful than the L, and you will want a car for the countryside trips the city does so well.
Shopping & style
Chicago is the better place to shop. The Magnificent Mile has flagships and vertical malls, Oak Street has the luxury labels, and the old Marshall Field's store on State Street, with its Tiffany ceiling, is worth seeing in its own right. Wicker Park and Andersonville add independent shops.
Philadelphia has no grand shopping street, just Walnut Street around Rittenhouse Square. In return it has character: Jewelers' Row, food gifts from Reading Terminal and cookware from the Italian Market. There is also no Pennsylvania sales tax on clothing, which helps on a trip out to the vast King of Prussia mall.
Affordability
Chicago is the dearer of the two, though neither is cheap. Its downtown hotels cost more than those in Center City, and they climb further in summer and when big conventions are in town. Chicago's steep hotel and sales taxes then add to every bill. A sit-down dinner with tax and tip is expensive in both cities, so most of the difference is in what you pay for your room.
Philadelphia leaves a little more in your pocket, partly because its centre is compact enough that a hotel there puts most of the sights within walking distance. On free sightseeing the two are roughly even. Chicago has its lakefront, beaches, Millennium Park and Lincoln Park Zoo, and Philadelphia has the Liberty Bell and Independence Hall. The headline art museums cost money in both: the Art Institute in Chicago, and the Barnes and the Philadelphia Museum of Art in Philadelphia, all charge full admission.
Live music & performing arts
Chicago has the wider stage and a sound of its own. Electric blues still plays in clubs on the North and South Sides, jazz rooms keep late sets, and Second City runs improv every night. The Lyric Opera has a full season, Goodman and Steppenwolf lead a theatre scene that reaches down to small storefront companies, and in summer there are free concerts at the Pritzker Pavilion.
Classical music is where the two meet as equals, with a world-class orchestra in each. Philadelphia's stage leans more classical overall: the ornate 1857 Academy of Music, recitals by Curtis Institute students and the Walnut Street Theatre, the oldest working theatre in the country. Its jazz and soul clubs are smaller affairs.
Wellness & relaxation
Chicago's century-old Russian-and-Turkish bathhouse in Wicker Park, with its scorching steam and cold plunges, gives it a bathing tradition that Philadelphia lacks. The warm glasshouses at Lincoln Park and Garfield Park are proper winter escapes too, though neither city is somewhere people go mainly to unwind.
Philadelphia has nothing beyond hotel and day spas, and the Korean-style bathhouses mean a drive to the suburbs. Its quiet moments happen outdoors instead, on a bench in one of Penn's leafy squares or on a walk in the Wissahickon gorge.
When should you go?
Pick your month. The climate figures are measured averages, not a forecast.
Chicago in July
Philadelphia in July
Daytime high, °C
Rainfall in the month, mm
Temperature and rainfall are climate normals, averaged over the years shown. Chicago: 1991-2020 normals, Chicago Midway Airport (14.5 km from centre). Philadelphia: 1991-2020 normals, Philadelphia International Airport (11.3 km from centre).
Both cities have proper four-season climates, but Chicago swings harder. Its winters are bitter, around 0°C by day in January, and the wind off the lake makes walking between sights a chore from December to March. Summer makes up for it. July and August are warm without being heavy, and the lake reaches about 23°C in August, so swimming from the city beaches works from late June into early September. The wettest weeks come in late spring, with about 121mm in May, and September is often the most comfortable month for exploring.
Philadelphia is milder in winter and a little hotter in summer, reaching about 31°C in July, when walking round Old City can feel sticky. Rain is spread fairly evenly through the year, with no real dry season. Late spring and early autumn are the sweet spots, with long sunny days from May to August and pleasant October afternoons around 20°C.
Which traveller are you?
On a food and nightlife trip, Chicago is the clear pick. Its neighbourhood cooking runs from Pilsen's Mexican kitchens to Devon Avenue's South Asian food, and the late licences mean a night in Wicker Park or River North can carry on into the early hours.
On a family trip with children, Chicago again has the edge. It has the Museum of Science and Industry, the dinosaurs, aquarium and planetarium side by side on the Museum Campus, a free lakeside zoo and lifeguarded summer beaches. The one thing to avoid is a winter visit.
On a trip with a tight budget, Philadelphia stretches the money further. The founding sights of Old City cost nothing, a cheesesteak or hoagie makes lunch, and bringing your own wine cuts the cost of dinner. Chicago's hotel taxes and convention-season rates bite harder.
Before you go
| Measure | Chicago | Philadelphia |
|---|---|---|
| Currency | US Dollar (USD) | US Dollar (USD) |
| Sockets | AB120 V, 60 Hz | AB120 V, 60 Hz |
| Driving side | Right | Right |
| Time zone | UTC-6, UTC-5 in summer | UTC-5, UTC-4 in summer |
| Emergency number | 911 | 911 |
| Elevation | 179 m | 12 m |
| Main airport | Chicago O'Hare International Airport (ORD)25 km from centre274 non-stop destinations | Philadelphia International Airport (PHL)11 km from centre129 non-stop destinations |
| Public holidays this year | 13 days | 12 days |
By the numbers
| Measure | Chicago | Philadelphia |
|---|---|---|
| City population | 2,746,388 | 1,603,797 |
| People per km² | 4,529 | 4,339 |
| Museums within 10 km | 44 | 54 |
| UNESCO World Heritage sites within 50 km | 1 | 1 |
| Swim season, months above 21 °C | 1 month | - |
Where else could you go?
Every comparison below shares a destination with this one, so you can follow Chicago or Philadelphia somewhere new.