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Illinois, United States

Chicago

The Windy City; Chi-Town; The Second City; City of Big Shoulders

Overall
6.5
Per day
$345 from $218

Best for:Road tripsCar-free travel

  • Drive
  • Train
  • Bus
  • Airport
  • EV charging
Directions

Best connected to Milwaukee 1 h 40 min by car

Overview

Lake Michigan runs along the edge of Chicago, and the lakefront shapes daily life more than anything else. About 2.7 million people live in the city, with more than nine million in the metro area, and it has the feel of a big city that stays practical about money. Visitors take an architecture cruise on the river, see the Bean in Millennium Park, spend an afternoon at the Art Institute or the Field Museum, and catch a Cubs game at Wrigley Field.

Costs are reasonable for a major city, with rent and home prices well below the coasts. Winters are brutally cold and windy, while summer is festival season, with Lollapalooza and the Pride Parade. Safety is uneven. The Loop and the lakefront are busy and well patrolled, but violence is concentrated in parts of the South and West Sides. Shootings have fallen recently, though rates remain above the national average.

Trip planning at a glance

Nearest airport
O'Hare Intl (ORD)

Highlights

  • Millennium Park and Cloud Gate (The Bean)
  • Art Institute of Chicago
  • Architecture river cruise
  • Navy Pier and lakefront
  • Willis Tower Skydeck
  • Field Museum and Museum Campus
  • Wrigley Field / Cubs game

Best connected to

Milwaukee

Wisconsin, United States ·

6.4
Distance
90 mi · 145 km
Drive
1 h 40 min
Train
likely (not verified) · 2 h 39 min
Bus
likely (not verified) · 2 h 40 min

adds beaches and historic sites

Indianapolis

Indiana, United States ·

7.1
Distance
180 mi · 290 km
Drive
3 h
Train
likely (not verified) · 5 h 7 min
Bus
likely (not verified) · 5 h 4 min

adds national & state parks and historic sites

St. Louis

Missouri, United States ·

5.9
Distance
300 mi · 483 km
Drive
4 h 15 min
Train
likely (not verified) · 7 h 59 min
Bus
likely (not verified) · 7 h 52 min

adds food scene and wineries & breweries

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Jacksonville (FL)

Florida, United States

Overall
7.0
Connector
7.8
Per day (mid-range)
$200

Road tripsCar-free travelFamilies

  • Drive
  • Train
  • Bus
  • Airport
  • EV charging

Peak: Spring through summer at the beaches, p…

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Kenosha

Wisconsin, United States

Overall
6.7
Connector
8.3
Per day (mid-range)
$154

NightlifeBeaches

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  • Train
  • Airport

Peak: Summer and holiday shopping weekends

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Sackville

New Brunswick, Canada

Overall
6.8
Connector
8.7
Per day (mid-range)
$133

Car-free travelOutdoors

  • Drive
  • Train
  • Bus
  • Airport
  • Camping

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Scores

Out of 10. Open any score to see how it’s worked out. “Data-based” scores come from published figures; “Hey! En Route estimate” scores are worked out from what we know about the city; “Hey! En Route rating” scores were set by our editors.

6.5/10Good
  • Connector Score8.2

    19 worthwhile cities within three hours; reachable by road, intercity train, intercity bus, air, and local transit; lodging and sights for an overnight stop. Hey! En Route estimate

  • Safety4.5

    About 670 violent crimes per 100,000 people a year; the US average is about 370. Data-based

  • Affordability5.7

    Cost of living index about 108, where the national average is 100. Data-based

  • Transportation10.0

    Reachable by: road, intercity train, intercity bus, air, and local transit. Hey! En Route estimate

  • Car-free friendliness7.0

    Intercity train or bus, plus local transit and walkability. Hey! En Route estimate

  • Walkability5.8

    Estimated from city size and transit; no walkable downtown noted. Hey! En Route estimate

  • Things to do6.9

    Known for 3 kinds of attraction, with 7 annual events listed. Hey! En Route estimate

  • Food & dining6.0

    Estimated from city size and dining listings. Hey! En Route estimate

  • Places to stay7.5

    Lodging at budget, mid-range and luxury prices. Hey! En Route estimate

  • Nature & outdoors3.5

    Known for lakes & rivers. Hey! En Route estimate

  • Scenic value4.8

    From its landscape: coast, mountains, lakes and parks. Hey! En Route estimate

  • Family friendliness4.4

    Zoos, aquariums, theme parks and museums, weighted by safety. Hey! En Route estimate

  • Solo-traveler friendliness4.7

    Safety, getting around without a car, hostels, and things to do. Hey! En Route estimate

  • Nightlife4.5

    Estimated from city size and live music. Hey! En Route estimate

  • Remote-work friendliness7.2

    City size, affordability, cafés and connections. Hey! En Route estimate

  • Road-trip convenience7.5

    19 worthwhile cities within three hours’ drive, plus parking, EV charging and RV options. Hey! En Route estimate

  • Train-trip convenience7.8

    Intercity train service, with 15 nearby cities reachable by rail. Hey! En Route estimate

  • Bus-trip convenience7.3

    Intercity buses, with 9 nearby cities reachable by bus. Hey! En Route estimate

City info

Country
United States
State / province
Illinois
Population
2,731,585
Metro area
9,434,123
Area
606 km²
Density
4,508 / km²
Elevation
181 m
Currency
USD
Local time
6:54 pm UTC-05:00
Power
Type A/B, 120V 60Hz
Drives on the
Right
Visitor info
choosechicago.com
Known as
The Windy City; Chi-Town; The Second City; City of Big Shoulders
Founded
1833 incorporated as a town (1837 as a city)
Languages
English; Spanish (~25-28% at home); Polish, Chinese, Tagalog and others
Airports
ORD (O'Hare Intl); MDW (Midway Intl)
Tipping
Restaurants 18-22%; taxis/rideshare 15-20%; bartenders $1-2/drink; hotel housekeeping $3-5/night; bellhop $1-2/bag

Community signals

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About this data

Pop: Census Vintage 2025. Hotel rate: Engine. Rent: Zillow. Crime: approximate aggregate plus 2025 trend reports.

Last verified September 25, 2026 · Source: Research spreadsheet · Editorial ·

Neighborhoods

8 areas to know, and who each one suits.

Wicker Park

Artsy

    Pilsen

    Colorful

      Hyde Park

      Academic

        Gold Coast

        Upscale

          Where to base yourself

          • The Loop and Magnificent Mile/River North (central)
          • Streeterville and Gold Coast (upscale, lakefront)
          • Lincoln Park or Wicker Park (local feel)
          • West Loop (dining)

          Suburbs and neighboring towns

          Evanston (12 mi; CTA Purple Line, Metra); Oak Park (9 mi; CTA Green Line, Metra); Forest Park (10 mi; CTA Blue Line); Cicero (8 mi; CTA bus, Metra, car); Berwyn (10 mi; Metra BNSF, car); Skokie (14 mi; CTA Yellow Line, car); Hammond IN (22 mi; South Shore Line train, car)

          What a visit costs

          Per person per day, with a room shared by two. Change anything below to fit your trip.

          Budget

          $218/day

          Lodging about $135 a night

          Mid-range

          $345/day

          Lodging about $240 a night

          Luxury

          $665/day

          Lodging about $550 a night

          Budget calculator

          Vehicle
          mpg

          These are estimates from typical prices, not quotes. Real costs vary with season, events, booking time and your own habits; taxes and fees are approximate.

          Cost of living

          For longer stays and relocation.

          Cost of living index
          108 (national average = 100)
          Typical 1-bedroom rent
          $2,100 a month
          Median home price
          $335,000
          Research notes

          Index roughly 105-110 (US = 100); 1BR rent ~$1,900-2,300

          Real estate

          Buying or renting long-term: prices, trends and the rules.

          Median home

          $335,000

          Mortgage calculator

          Median home value ~$320k-350k; median rent ~$2,000 (Zillow); steady, modest appreciation

          Research notes on prices and seasons

          Avg hotel ~$233/night (Engine). Budget $100-170; mid $180-300; luxury $400-700+. Visitor budget ~$150-300/person/day excluding lodging

          Where to stay

          Which part of town suits which kind of trip.

          • The Loop and Magnificent Mile/River North (central)
          • Streeterville and Gold Coast (upscale, lakefront)
          • Lincoln Park or Wicker Park (local feel)
          • West Loop (dining)

          Places to stay

          6 listings in Chicago, ranked by traveller reviews. Featured listings are marked.

          Top sights

          • Millennium Park and Cloud Gate (The Bean)
          • Art Institute of Chicago
          • Architecture river cruise
          • Navy Pier and lakefront
          • Willis Tower Skydeck
          • Field Museum and Museum Campus
          • Wrigley Field / Cubs game

          Known for: Lakes & riversMuseums & galleriesPro sports

          Things to do

          9 listings in Chicago, ranked by traveller reviews. Featured listings are marked.

          See what’s on: events and festivals

          Food & nightlife

          6 listings in Chicago, ranked by traveller reviews. Featured listings are marked.

          Events

          Dated events will appear here as they’re added.

          Every year

          • Chicago Auto Show (Feb)
          • St. Patrick's Day Parade and river dyeing (Mar)
          • Pride Parade (Jun)
          • Taste of Chicago (Jul/Sep)
          • Lollapalooza (late Jul/early Aug)
          • Chicago Air and Water Show (Aug)
          • Chicago Marathon (Oct)

          Official events calendar ↗

          Safety information is a guide from public data and our research, not a guarantee. Conditions change; check local news and official advice before you go.

          4.5

          Fair · Data-based

          About 670 violent crimes per 100,000 people a year; the US average is about 370.

          Safety overview

          Violent crime ~540-800 per 100k depending on source; homicides and shootings fell substantially in 2024-2025 to a decade-plus low but remain above the national average. Risks: phone snatching and petty theft downtown/transit, car break-ins, rideshare impersonation. Hospitals: Northwestern Memorial, Rush, UChicago Medicine. Extreme winter cold and wind chill; summer heat

          Local notes

          Specific places where extra care is worthwhile, especially at night. Most visits are trouble-free.

          Downtown, Loop, Magnificent Mile and lakefront are busy and well patrolled. Caution at night in parts of the South and West Sides (Englewood, West Garfield Park, Austin, North Lawndale), where violence is concentrated; late-night CTA trains and stations; large events and holiday weekends

          Safety & health

          Health

          • Hospital (ER)Northwestern Memorial
          • Hospital (ER)Rush
          • Hospital (ER)UChicago Medicine
          Official visitor information
          choosechicago.com

          Last verified September 25, 2026 · Source: Research spreadsheet · Editorial ·

          Local directory

          24 listings in Chicago, ranked by traveller reviews. Featured listings are marked.

          Nearby

          21 places outside Chicago, within an easy drive.

          Nearby cities and connections

          Find the next city worth adding to your trip from Chicago: how far, how long, and how to get there.

          Kenosha

          Wisconsin, United States ·

          6.7
          Distance
          55 mi · 89 km
          Drive
          1 h
          Train
          likely (not verified) · 1 h 43 min

          Racine

          Wisconsin, United States ·

          6.4
          Distance
          70 mi · 113 km
          Drive
          1 h 15 min
          Train
          likely (not verified) · 2 h

          Rockford

          Illinois, United States ·

          6.4
          Distance
          90 mi · 145 km
          Drive
          1 h 25 min
          Train
          likely (not verified) · 2 h 36 min
          Bus
          likely (not verified) · 2 h 38 min

          Milwaukee

          Wisconsin, United States ·

          6.4
          Distance
          90 mi · 145 km
          Drive
          1 h 40 min
          Train
          likely (not verified) · 2 h 39 min
          Bus
          likely (not verified) · 2 h 40 min

          South Bend

          Indiana, United States ·

          6.0
          Distance
          95 mi · 153 km
          Drive
          1 h 40 min
          Train
          likely (not verified) · 2 h 23 min
          Bus
          likely (not verified) · 2 h 25 min

          Elkhart

          Indiana, United States ·

          5.8
          Distance
          120 mi · 193 km
          Drive
          2 h
          Train
          likely (not verified) · 2 h 48 min

          Kalamazoo

          Michigan, United States ·

          6.5
          Distance
          145 mi · 233 km
          Drive
          2 h
          Train
          likely (not verified) · 3 h 27 min
          Bus
          likely (not verified) · 3 h 27 min

          Lafayette (IN)

          Indiana, United States ·

          6.0
          Distance
          125 mi · 201 km
          Drive
          2 h
          Train
          likely (not verified) · 3 h 27 min
          Bus
          likely (not verified) · 3 h 27 min

          Champaign

          Illinois, United States ·

          6.0
          Distance
          135 mi · 217 km
          Drive
          2 h 15 min
          Train
          likely (not verified) · 3 h 58 min

          Madison

          Wisconsin, United States ·

          6.5
          Distance
          150 mi · 241 km
          Drive
          2 h 30 min
          Train
          likely (not verified) · 3 h 51 min
          Bus
          likely (not verified) · 3 h 50 min

          Carmel

          Indiana, United States ·

          5.5
          Distance
          180 mi · 290 km
          Drive
          3 h
          Bus
          likely (not verified) · 4 h 44 min

          Springfield (IL)

          Illinois, United States ·

          5.2
          Distance
          200 mi · 322 km
          Drive
          3 h
          Train
          likely (not verified) · 5 h 30 min
          Bus
          likely (not verified) · 5 h 27 min

          Grand Rapids

          Michigan, United States ·

          6.2
          Distance
          180 mi · 290 km
          Drive
          3 h
          Train
          likely (not verified) · 3 h 56 min
          Bus
          likely (not verified) · 3 h 56 min

          Indianapolis

          Indiana, United States ·

          7.1
          Distance
          180 mi · 290 km
          Drive
          3 h
          Train
          likely (not verified) · 5 h 7 min
          Bus
          likely (not verified) · 5 h 4 min

          Fort Wayne

          Indiana, United States ·

          7.4
          Distance
          175 mi · 282 km
          Drive
          3 h 19 min est.
          Train
          likely (not verified) · 4 h 23 min
          Bus
          likely (not verified) · 4 h 22 min

          Muncie

          Indiana, United States ·

          5.7
          Distance
          206 mi · 332 km
          Drive
          3 h 54 min est.
          Bus
          likely (not verified) · 5 h 4 min

          Lansing

          Michigan, United States ·

          6.1
          Distance
          210 mi · 338 km
          Drive
          3 h 58 min est.
          Train
          likely (not verified) · 5 h 12 min
          Bus
          likely (not verified) · 5 h 9 min

          Detroit

          Michigan, United States ·

          6.6
          Distance
          280 mi · 451 km
          Drive
          4 h
          Train
          likely (not verified) · 7 h 15 min
          Bus
          likely (not verified) · 7 h 9 min

          St. Louis

          Missouri, United States ·

          5.9
          Distance
          300 mi · 483 km
          Drive
          4 h 15 min
          Train
          likely (not verified) · 7 h 59 min
          Bus
          likely (not verified) · 7 h 52 min

          Green Bay

          Wisconsin, United States ·

          5.9
          Distance
          229 mi · 368 km
          Drive
          4 h 20 min est.
          Bus
          likely (not verified) · 5 h 36 min

          Ann Arbor

          Michigan, United States ·

          6.2
          Distance
          252 mi · 405 km
          Drive
          4 h 46 min est.
          Train
          likely (not verified) · 6 h 11 min
          Bus
          likely (not verified) · 6 h 7 min

          Toledo

          Ohio, United States ·

          6.0
          Distance
          264 mi · 425 km
          Drive
          5 h est.
          Train
          likely (not verified) · 6 h 29 min
          Bus
          likely (not verified) · 6 h 25 min

          Dayton

          Ohio, United States ·

          5.5
          Distance
          290 mi · 466 km
          Drive
          5 h 29 min est.
          Bus
          likely (not verified) · 7 h

          Windsor

          Ontario, Canada ·

          6.8
          Distance
          297 mi · 478 km
          Drive
          5 h 37 min est.
          Train
          likely (not verified) · 7 h 15 min

          Warren

          Michigan, United States ·

          5.3
          Distance
          299 mi · 481 km
          Drive
          5 h 40 min est.
          Bus
          likely (not verified) · 7 h 12 min

          Times marked “est.” are estimates: drives use typical road distances at highway speeds, and train or bus times assume both cities have service. Always check a route planner and timetables before you travel.

          Route ideas

          Suggested by Hey! En Route from the best-connected next stops. Save one to your routes and make it your own.

          2-day trip

          Chicago (1 night)

          3-day trip

          Chicago (1 night) → Milwaukee (1 night)

          About 89 mi, 1 h 51 min of travel

          5-day trip

          Chicago (2 nights) → Milwaukee (1 night) → Appleton (1 night)

          About 196 mi, 3 h 55 min of travel

          7-day trip

          Chicago (2 nights) → Milwaukee (1 night) → Appleton (1 night) → Madison (1 night)

          About 300 mi, 6 h 9 min of travel

          10-day trip

          Chicago (2 nights) → Milwaukee (2 nights) → Appleton (1 night) → Madison (1 night) → Kenosha (1 night)

          About 414 mi, 8 h 31 min of travel

          Suggested city pairs

          Building your own routes is part of Hey! En Route Plus. See what’s included

          Community signals

          Not enough responses yet to show a trend.

          Chicago City Circle

          For people considering Chicago, visiting soon, living there for a while, or comparing it with somewhere else.

          Sign up to join

          No discussions yet. Be the first to share something useful.

          Share experience, not guesses presented as fact, and keep contact details out of posts. Community guidelines

          The newsletter

          Postcards from the road, every other week

          New city guides, events worth planning a trip around, and the places worth the detour. Pick your topics, or leave them all unticked for everything.