Chicago, IL
Chicago travel guide
Big-shoulders architecture and a lakefront for everyone
- Airports
- ORD O'Hare International Airport · MDW Chicago Midway International Airport
- Region
- US Midwest
- Best time to visit
- June–September is warm, with festivals almost every weekend (and the highest hotel rates).
- Shortest flight
- 2h 10m from Atlanta
- Round trips from
- $62 (live)
- Time zone
- America/Chicago
About Chicago
Chicago's downtown Loop sits on Lake Michigan with 18 miles of public beaches and trails. Millennium Park, the Art Institute, the Riverwalk and an architecture boat tour fill a day; the North Side neighborhoods (Wicker Park, Logan Square, Lincoln Park) and the South Side's Hyde Park and Pilsen fill the rest.
Getting in: both airports have direct CTA trains to downtown. From O'Hare the Blue Line takes 40–45 minutes ($5); from Midway the Orange Line takes about 25 minutes ($2.50). Taxis from O'Hare run $45–$60 to the Loop, rideshares $35–$55. Midway is the Southwest hub and often cheaper for domestic flights.
Stay in the Loop or River North for convenience, Wicker Park or Logan Square for restaurants and nightlife, and Lincoln Park for a residential base near the lake. Deep-dish, Italian beef and a Chicago dog cost $10–$20; the tasting-menu scene (Alinea, Smyth) sits at the other extreme. Tip 18–20%.
Best time to visit
June–September is warm, with festivals almost every weekend (and the highest hotel rates). May and October are cool and cheaper; winter is cold but hotels are a bargain.
Where to stay
Neighborhoods our travelers like: The Loop, River North, Wicker Park, Logan Square, Lincoln Park.
Flights to Chicago: typical round-trip fares
What economy round trips to ORD usually cost from major US cities, alongside the lowest live fare we can see in the next 90 days. Prices are per traveler and include taxes.
| From | Flight time | Typical fare | Lowest live fare | Actions |
|---|---|---|---|---|
| New York (JFK) | 2h 45m | $128 | $82 · Tue, Nov 3 | Search dates → |
| Los Angeles (LAX) | 4h 5m | $168 | $146 · Tue, Nov 10 | Search dates → |
| Dallas (DFW) | 2h 35m | $138 | $82 · Tue, Nov 10 | Search dates → |
| Atlanta (ATL) | 2h 10m | $118 | $62 · Tue, Nov 3 | Search dates → |
| Boston (BOS) | 2h 45m | $128 | $77 · Tue, Oct 13 | Search dates → |
| Denver (DEN) | 2h 30m | $108 | $98 · Tue, Nov 10 | Search dates → |
Typical fares are editorial estimates for economy round trips booked 3–8 weeks out. Live fares refresh several times a day and are shown for the cheapest departure date we found.
What to do in Chicago
The places our editors send first-time visitors.
- 1
Chicago Architecture Center river cruise
The 90-minute boat tour along all three branches of the river is the best introduction to the city's skyline.
- 2
Millennium Park and the Art Institute
Cloud Gate ('the Bean'), free summer concerts at the Pritzker Pavilion, and one of the great art collections across the street.
- 3
Wrigley Field
A Cubs game at the 1914 ballpark, then the bars of Wrigleyville; tickets from $20 on weekdays.
- 4
The Riverwalk and Navy Pier
A 1.25-mile promenade of cafés and kayak rentals ending near the lake; Navy Pier has summer fireworks Wednesdays and Saturdays.
- 5
Neighborhood food crawls
Pilsen for tacos and murals, Devon Avenue for South Asian food, Logan Square for the city's most creative restaurants.
Chicago weather by season
Average highs and lows in °F, with what each season means for fares and crowds.
Winter
33° / 20°
Cold, windy, snowy; cheapest hotels.
Spring
57° / 41°
Unpredictable; layers required.
Summer
82° / 65°
Warm and lively — beach and festival season.
Fall
62° / 46°
Crisp and colorful; marathon in October.
Travel tips for Chicago
- Fly into Midway for Southwest fares and a shorter train ride; O'Hare has more nonstops and international flights.
- Buy a Ventra day pass ($5) — CTA trains reach both airports and most neighborhoods.
- Museum free days: the Art Institute and Field Museum have Illinois-resident days, but many museums offer discounted evening hours to all.
- Winter fares and hotel rates drop 30–50%; pack for wind chills well below freezing.
- Book the architecture cruise a few days ahead in summer; late-afternoon departures have the best light.
Chicago flights: frequently asked questions
O'Hare or Midway — which should I choose?
O'Hare (ORD) has the most flights, including all international service; Midway (MDW) is Southwest's hub, closer to downtown and often cheaper. Both have direct CTA trains to the Loop.
How do I get from O'Hare to downtown Chicago?
The CTA Blue Line runs 24/7 from Terminals 1–3 and takes 40–45 minutes to the Loop for $5. Taxis and rideshares take 30–60 minutes depending on traffic and cost $35–$60.
Is Chicago worth visiting in winter?
If you can handle the cold, yes: hotels are half price, museums are quiet, and the holiday lights and Christkindlmarket in December are excellent. Pack a real winter coat.
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