Chicago is a city of extremes: world-class museums and architecture alongside genuine winter cold that surprises first-time visitors. The CTA L train system connects the city efficiently, O’Hare is one of the world’s busiest airports (and the L goes there directly), and the food scene ranks among America’s best. Here is the practical information that guidebooks skip. For trip timing, see best time to visit Chicago.
Chicago Travel Tips: Airports and Arrival
Chicago has two major airports. O’Hare International (ORD) is 27km northwest of downtown in the Rosemont area, handling the majority of domestic and international flights. It is a major hub for United Airlines and American Airlines. Midway International (MDW) is 16km southwest of downtown on the city’s Southwest Side, primarily serving Southwest Airlines with domestic flights. If your ticket says “Chicago” without specification, assume O’Hare.
Getting from O’Hare to Downtown
The CTA Blue Line runs directly from O’Hare Terminal 2 (follow signs to “CTA Trains” in the lower level of Terminal 2, connected from Terminals 1 and 3 via pedestrian walkways, from Terminal 5 via the free Airport Transit System). Trains run every 6-12 minutes, 24/7. Journey to Clark/Lake in the Loop: 40-45 minutes, US$5 (the US$2.50 base fare plus a US$2.50 O’Hare surcharge). Buy a Ventra Card at the station vending machine (US$5 for the card, then load value). A taxi from O’Hare to downtown costs US$40-55 flat rate (metered rates were eliminated for downtown trips), taking 30-60 minutes depending on traffic. Uber/Lyft from O’Hare: US$35-50. Ride-share pickup is at designated zones on the upper level. The where to stay in Chicago guide matches hotels to L stops.
Getting from Midway to Downtown
The CTA Orange Line runs from Midway directly to the Loop. Journey to Clark/Lake: 25-30 minutes, US$2.50. The station is connected to the airport terminal via an enclosed walkway. Trains run every 8-15 minutes from approximately 4am to 1am. A taxi from Midway to downtown costs US$30-40, taking 20-35 minutes. Uber/Lyft: US$25-35.
Chicago Travel Tips: Getting Around the CTA
The Chicago Transit Authority (CTA) operates 8 L (elevated) train lines and 129 bus routes. The L uses a color-coded system: Red and Blue Lines run 24/7. Brown, Green, Orange, Pink, and Purple Lines run approximately 4am-1am. Yellow Line runs between Howard and Skokie. The downtown area inside the “Loop” (the rectangle formed by the elevated tracks at Lake, Wabash, Van Buren, and Wells Streets) is served by all lines. Buy a Ventra Card (US$5 purchase fee) at any L station or online, then load value. Single rides: US$2.50 for L, US$2.25 for bus. 1-day pass: US$5 (good value at 2+ rides). 3-day pass: US$15. 7-day pass: US$20. Transfers between bus and L within 2 hours cost US$0.25. Buses accept cash but require exact change (US$2.25) and do not accept Ventra transfers from cash payments.
Taxis are plentiful downtown and can be hailed on the street. Flagfall: US$3.25, with US$2.25 per mile and US$0.25 per 36 seconds of waiting time. A typical 2-mile downtown trip costs US$10-15. Uber and Lyft are ubiquitous and typically 5-15% cheaper than taxis. The Chicago neighborhoods guide identifies the best L stops for each area.
Chicago Travel Tips: Money, Tipping and Costs
US Dollar (USD). Credit cards are universally accepted, even for small purchases. Tipping is standard and expected: restaurants 18-22% on the pre-tax total (check for automatic gratuity on parties of 6+), bars US$1-2 per drink or 15-20% of tab, hotel housekeeping US$2-5 per night, bellhops US$2 per bag, taxi/ride-share 15-20%. Sales tax in Chicago is 10.25% (combined state, county, and city), among the highest in the US. This is added at the register, not included in displayed prices. An additional 0.5% restaurant tax applies in the downtown area.
Daily budget estimates (summer): backpacker US$80-120 (hostel + CTA + casual meals), mid-range US$250-400 (4-star hotel + mix of restaurants + attractions), luxury US$500+ (5-star + fine dining). Winter hotel rates drop 40-50%, making mid-range budgets go much further.
Chicago Travel Tips: Winter Survival Guide
Chicago winters are not to be underestimated. January averages -1 C (31 F) during the day and -9 C (16 F) at night, with wind chills regularly dropping to -25 C (-13 F). The infrastructure is built for this: the Pedway system connects 40+ blocks of downtown buildings via heated underground walkways. Download the Chicago Pedway map app before your trip. Key winter gear: insulated waterproof boots with good traction (sidewalks can be icy for days after snow), a windproof outer layer, thermal base layers, and accessories covering ears, neck, and hands (the wind is the real enemy). The L trains run through virtually all winter weather. The Chicago Architecture Center runs indoor walking tours of the Pedway and hotel lobbies (US$25). Most Chicago museums are within a 10-minute indoor walk of an L station.
Chicago Travel Tips: Safety
Chicago’s reputation for crime is concentrated in specific neighborhoods on the South and West Sides that tourists rarely visit. The downtown area (Loop, River North, Streeterville), the Near North Side, and the North Side neighborhoods along the L lines are as safe as any major US city center. Standard urban precautions apply: avoid deserted L cars late at night (ride in the front car with the train operator), stay aware of your surroundings, and avoid displaying valuables on the L. The lakefront trail is well-populated and safe during daylight hours; use the CTA or Uber after dark rather than walking the trail alone. Hyde Park is generally safe during the day, particularly around the university campus, but use a ride-share after dark rather than waiting at isolated L or Metra stations.
Chicago Travel Tips: Suggested Hotels in Chicago
The Langham Chicago
5-star luxury in a Mies van der Rohe riverfront tower. Outstanding spa, river views, and a location that bridges the Loop and River North. Best for luxury travelers and special occasions. Check rates and availability
The Palmer House Hilton
Historic 1871 Beaux-Arts hotel in the Loop with one of the most impressive hotel lobbies in America. The location and character at mid-range prices make it excellent value. Best for first-time visitors wanting central location and history. Check rates and availability
Freehand Chicago
Design-forward hostel/hotel hybrid in River North with the acclaimed Broken Shaker bar. Private rooms from US$120-180, dorms from US$40. Best for solo travelers and budget-conscious creatives. Check rates and availability
For complete neighborhood hotel listings, see where to stay in Chicago. The Chicago events and festivals calendar covers seasonal booking strategies.
