Layover in Midway (MDY): Complete Guide to Chicago & Airport

Chicago Midway International Airport (MDY) is one of the busiest airports in the United States and serves as a major hub for Southwest Airlines. Located just 10 miles southwest of downtown Chicago, Midway offers excellent connectivity to the vibrant city beyond its terminals. Whether you have a short 2-hour layover or a full day to explore, this guide will help you make the most of your time at MDY.

Before You Leave the Airport

Getting to Chicago from Midway

Midway’s location makes it easy to reach downtown Chicago and surrounding neighborhoods. Here are your main transit options:

Transit Option	Time to Downtown	Cost	Best For
CTA Orange Line (Train)	~30-40 minutes	$5	Budget travelers, direct access to Loop
Taxi/Rideshare (Uber/Lyft)	~20-30 minutes	$25-45	Groups, luggage, convenience
Rental Car	~20-30 minutes	$40-80+/day	Longer layovers, exploring suburbs

Pro Tip: The CTA Orange Line is the most economical option and runs 24/7. Download the CTA app before landing for real-time train schedules.

What to Do During Your Layover

Short Layover (2-4 Hours)

If you’re short on time, stay near the airport or explore Midway’s immediate surroundings:

• Grab a meal: Midway has food options throughout the terminals. For better prices and variety, head to the food court rather than sit-down restaurants
• Rest: Find a quiet gate area or seating zone to relax. Check SleepingInAirports.net for the best spots to rest at MDY
• Shop: Browse duty-free shops and retail stores in the terminals
• Freshen up: Use airport restrooms and facilities to refresh before your next flight

Medium Layover (4-8 Hours)

With 4-8 hours, you can venture into Chicago’s nearby neighborhoods:

• Pilsen: Just south of Midway, this vibrant neighborhood features street art, Mexican restaurants, and galleries. Perfect for a 2-3 hour exploration
• Bridgeport: Historic neighborhood with local cafes and shops, easily accessible via CTA
• Midway Plaisance Park: Green space near the University of Chicago, about 15 minutes from the airport

Long Layover (8+ Hours)

With a full day or overnight layover, explore downtown Chicago:

• The Loop: Chicago’s downtown core with iconic architecture, museums, and the Chicago River. Take the Orange Line directly there
• Millennium Park: Free public park featuring Cloud Gate (“The Bean”), fountains, and open-air concerts
• Art Institute of Chicago: World-class museum with American and European masterpieces
• Navy Pier: Waterfront attraction with dining, entertainment, and lake views
• Museum Campus: Home to the Field Museum, Shedd Aquarium, and Adler Planetarium
• Wicker Park: Trendy neighborhood with boutiques, coffee shops, and street art

Luggage Storage: If you’re leaving the airport, store your luggage with Bounce, Stasher, or LuggageHero. Typical cost: $5-10 per bag per day – much cheaper than airport lockers.

Quick Layover Tips

• Download offline maps: Use Google Maps or Maps.me before landing. Airport WiFi can be unreliable
• Pack a layover bag: Keep snacks, entertainment, a change of clothes, and toiletries in your carry-on for easy access
• Bring an empty water bottle: Fill it after security to stay hydrated and save money
• Factor in return time: Budget 2.5-3 hours before international departures and 60 minutes before domestic flights when returning to MDY
• Use a Wise or Revolut card: Get the best exchange rates with zero markup instead of airport currency counters

Frequently Asked Questions

Can I leave MDY airport during a layover?

Yes, you can leave Midway during a layover if you have a connecting flight. However, you’ll need to clear immigration (if arriving internationally), collect your luggage, and recheck it for your next flight. For domestic connections, allow at least 2-3 hours total layover time. For international connections, budget 3-4 hours minimum. Always factor in security screening time when returning to the airport.

What is there to do at MDY during a layover?

At Midway itself, you can eat at food courts and restaurants, shop at retail stores, or rest in quiet gate areas. If you leave the airport, nearby Pilsen offers street art and Mexican cuisine (2-3 hours), while downtown Chicago is 30-40 minutes away via CTA Orange Line. Major attractions include Millennium Park, the Art Institute, Navy Pier, and the Loop’s iconic architecture.

How long of a layover do I need at MDY?

For domestic connections: 60-90 minutes minimum. For international connections: 2-3 hours minimum. To explore Chicago: 4+ hours recommended. To visit downtown Chicago: 8+ hours ideal. Always add extra time for immigration, security, and unexpected delays.

Are there lounges at MDY?

Yes, Midway has airport lounges available. You can access them with a Priority Pass membership (covers 1,400+ lounges worldwide), airline elite status, or a premium credit card. One-time day passes are available: Alaska ~$39, American ~$45, Delta ~$49, United ~$59. Check with your airline for specific lounge locations and access requirements.

Traveler-Specific Tips

For Families

• Pack a ‘layover bag’ inside your carry-on with snacks, entertainment, a change of clothes, and basic toiletries
• Most major airports have baby care rooms with changing tables, bottle warmers, and nursing areas – ask at information desks
• Download offline entertainment before your layover; airport WiFi may be slow or time-limited
• Bring an empty water bottle to fill after security – staying hydrated helps kids manage jet lag

For Solo Travelers

• Download offline maps (Google Maps or Maps.me) before landing – essential for navigating Chicago without data
• Keep your passport, phone, and wallet in a cross-body bag or hidden money belt when exploring the city
• Share your location with a trusted contact when exploring Chicago solo
• Consider getting an eSIM before traveling (Airalo, Holafly) for instant data without hunting for WiFi
• Rule of thumb: need 6+ hours total layover to leave the airport (1hr immigration + 2-3hr return buffer + explore time)

For Groups

• Add 15-30 minutes ‘group tax’ to all time estimates – groups move slower through immigration, security, and transit
• Designate a ‘group leader’ before the layover who manages timing, headcount, and communication