Solo travel in Chicago

Solo travel tips

• Eat at the bar in West Loop and River North restaurants; walk-in bar seats are often available when tables are booked out.
• The Chicago Architecture Center runs docent-led walking tours that are a good way to meet other travellers.
• Stay in River North, the Loop or Wicker Park for easy L access and plenty of places to eat alone.
• Late at night, ride in busier carriages, keep your phone out of sight near the doors and use ride-hailing from quiet stations.
• Divvy bikes and the Lakefront Trail make a self-guided half-day along the lake easy.

Where to stay

Great on your own

Museum · The Loop

Art Institute of Chicago

Start with the Impressionists on the second floor before tour groups arrive, then take the Modern Wing's Nichols Bridgeway straight into Millennium Park.

Time needed

3–4 hours

Cost

Mid-priced

• Iconic
• Art
• Rainy day
• History

Experience · Chicago River

Chicago Architecture Center river cruise

Sit on the open upper deck and bring a layer even in summer; it is several degrees cooler on the water.

Time needed

About 75–90 minutes

Cost

Mid-priced

• Iconic
• Architecture
• Views
• Couples
• Photo spot

Viewpoint · The Loop

Willis Tower Skydeck

Check the visibility before buying; low cloud can hide the view completely, and a late-afternoon visit gives you daylight and sunset in one ticket.

Time needed

1.5–2 hours

Cost

Mid-priced

• Iconic
• Views
• Kids

Museum · Museum Campus

Field Museum

Arrive at opening and do the Field in the morning; the Shedd is a five-minute walk away for the afternoon.

Time needed

3–4 hours

Cost

Mid-priced

• Kids
• Rainy day
• History
• Iconic

Landmark · Wrigleyville

Wrigley Field

Day games are a Chicago tradition; take the Red Line to Addison, as driving and parking around the ballpark are difficult.

Time needed

3–4 hours for a game

Cost

Mid-priced

• Iconic
• History
• Kids

Viewpoint · Streeterville

360 Chicago observation deck

Pick this over the Skydeck if you want lake and beach views; the Skydeck looks more over the city grid and the west.

Time needed

1 hour

Cost

Mid-priced

• Views
• Couples
• After dark

Meeting people

• Randolph Street restaurant row — The West Loop's Randolph Street and Fulton Market are lined with chef-driven restaurants in former warehouses. Book a few weeks ahead for weekend dinners, or try the bar seats that many places keep for walk-ins.
• Devon Avenue — On the far North Side, Devon Avenue is one of the largest South Asian commercial streets in the US, with Indian and Pakistani restaurants, sweet shops and sari stores, reached by bus from the Red Line.
• Lincoln Park blues bars — Kingston Mines and B.L.U.E.S. face each other on North Halsted Street and play live Chicago blues until late.
• Uptown — Home to the Green Mill jazz lounge and the Aragon Ballroom concert hall, on the Red Line north of Wrigleyville.

Sensible precautions

The main visitor areas are busy and generally comfortable, but phone snatching and pickpocketing happen on the L and at crowded sights, so keep valuables out of sight near train doors. Swim only at beaches when lifeguards are on duty, as Lake Michigan can have dangerous currents, and in winter dress for wind chill along the lake.

Emergency number

911 (police, fire, ambulance)

Staying connected

Free Wi-Fi is common in cafés, public libraries and at O'Hare; US prepaid SIMs and eSIMs are easy to buy.

Questions travellers ask