MDW · Layover Guide
Chicago
Stop in Chicago.
Best layover: 3–36h
LayoverScore™
Base city score. Your route score varies by savings and timing.
Exit realism
Comfortable window
Enough room in Chicago for a real stop. Keep the buffer at the end anyway.
Landside playbook
If time slips
- Drop the last stop. Go straight to the train, taxi rank, or ride pickup you already chose.
- Add 15 minutes to map ETAs for the return leg at rush hour.
- One ticket for the whole trip protects you when the inbound is late. Separate tickets do not.
Worth knowing
- Do not stack three stops. One solid block in the city beats a rushed loop.
- Do not treat one map time as gospel for immigration lines. Pad on your first pass through this hub.
Planning a stop in Chicago?
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Places to stay
Search hotelsLayoverScore™ breakdown
Score 62 · Discover 49 · Ease 6
Why Chicago scores 62
Getting there
CTA Orange Line $2.5 · Rideshare (Uber/Lyft) $28
min to center
metro- 01CTA Orange Line to downtown (25-30 min, $2.50)
- 02Rideshare to Loop (20-35 min depending on traffic)
- 03Taxi to downtown (~$35-45)
- 01Deep-dish pizza at Lou Malnati's or Pequod's
- 02The Art Institute of Chicago's Impressionist collection
- 03Millennium Park and Cloud Gate (The Bean)
- 04Chicago-style hot dogs at Portillo's
- 05Architecture boat tour on the Chicago River
Experiences in Chicago
Timed tours and tickets for Chicago are listed on our partner site.
Open listingsOpens in a new tab.
Need a room for your layover? Browse hotels near the airport.
Where to stay →Drop your luggage. Don't drag it around the city.
Vertoe - Loop Location
Downtown Chicago (multiple spots)
$6/bag
0 min walk
LuggageHero Chicago
Various downtown hotels and shops
$6/bag
0 min walk
Chicago Union Station
Union Station (Canal & Adams)
$10/day
5 min walk
From the terminal to the good part.
CTA Orange Line
to downtown
Runs every 8-12 min, direct to Loop stations
28 min
$2.50
Rideshare (Uber/Lyft)
to downtown
Can be 40+ min during rush hour
25 min
$28.00
Taxi
to downtown
Flat rate not available; metered
25 min
$40.00
Chicago CityPASS
Shedd Aquarium, Skydeck Chicago, Field Museum + 2 more
Valid 9 consecutive days; best for 10+ hour layovers
$114
per day
Getting there
Get an Uber from the airportAt the airport
- 01Reilly's Daughter Irish Pub for local craft beers
- 02Midway Boulevard food court with Chicago-style options
- 03Harry Caray's Tavern for sports bar atmosphere
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