Few things beat the feeling of sneaking in a city visit during a layover in Chicago. Chicago Midway International Airport is well-positioned for exactly that — downtown is reachable in about 85 minutes. Here’s what you need to know to make it happen smoothly.
Pre-Departure Checklist
Three things to verify before you walk out of MDW:
- Can you legally enter United States? Some nationalities need a visa even for a few hours. Check your passport’s validity too.
- Do you have enough time? With a 85-minute journey each way by CTA Orange Line, you’ll want at least 5-6 hours total to make the trip worthwhile.
- How will you pay? Local currency is the USD. You’re in USD territory, so no currency conversion needed.
Airport to City: Your Transport Options
The most straightforward way into Chicago is the CTA Orange Line, which takes about 85 minutes. This is generally the best option for layover travelers — it’s reliable and you won’t get stuck in traffic.
A taxi or ride-share will also get you there, typically in 105 minutes depending on conditions, but expect to pay significantly more. If time is tight, the CTA Orange Line is usually the smarter call.
Layover Budget Breakdown
You don’t need a fortune for a layover outing. Here’s a realistic estimate for Chicago:
Transport to the city and back runs about $10 USD. A sit-down meal averages around $20 USD. Add $10 for a coffee, snacks, or a small souvenir, and you’re looking at roughly $40 USD total.
Cards are increasingly accepted in Chicago, but cash is still useful for smaller purchases.
Luggage Storage at MDW
You can store your luggage at Not available due to security regulations common at U.S. airports.. Rates typically depend on bag size and duration.
If the airport lockers are full or inconveniently located, services like Bounce and Stasher list verified storage spots in and around Chicago as well.
What to See and Do in Chicago
With limited time, focus on what’s accessible. In Chicago, two standouts are:
- Millennium Park (Cloud Gate “The Bean”) — Nice green space that’s easy to enjoy without a tight schedule.
- Chicago Riverwalk — Just walking around here gives you a feel for the local vibe.
Both are realistic options even if you only have a few hours to spare.
Not every layover calls for a city trip. If you’re staying at MDW, check out Hilton Chicago/Midway Airport or Midway Art Program to keep yourself occupied.
Where to Eat
In Chicago
If you make it into town, Lou Malnati’s Pizzeria (Loop) is a good bet for a proper meal. For something different, try Portillo’s Hot Dogs (Loop).
Inside MDW
If you’re staying in the terminal, Harry Caray’s Seventh Inning Stretch is your main option. Reilly’s Daughter works too if you want something quick.
Where to Rest During Your Layover
Not every layover involves sightseeing. If you’d rather rest, MDW has seating areas throughout the terminal, though comfort levels vary. Grab a neck pillow and stake out a quiet corner.
Airport lounges — accessible via day pass, credit card perks, or services like Priority Pass — typically offer reclined seating, showers, and a quieter environment.
Staying Connected
You’ll find free WiFi at MDW for basic browsing. If you plan to navigate Chicago or use ride-hailing apps, having mobile data is much more convenient. Consider setting up an eSIM through a provider like Airalo or Holafly before your trip — it takes a few minutes and saves you from hunting for SIM card kiosks.
Final Thoughts
A layover in Chicago with time to spare is really an invitation to explore. Chicago may not have been on your original itinerary, but sometimes those surprise stops become the best part of a trip.
Just remember: set an alarm, know your gate, and leave time for security. Everything else is an adventure.
Nearby Layover Guides
Disclaimer: Visa rules, transport schedules, and prices change. Always verify details with official sources and your airline before leaving the airport.