Visible cost: $1,373(66/66 activities shown)
Day 1
Day 1 · Departure Day (New York)
$384
Finish packing, double-check ID / documents
Rideshare to LaGuardia (LGA), Terminal B (~30–45 min)
Arrive LGA, check in & drop bag
Security screening (TSA PreCheck lane)
Coffee & a bite near the gate
Boarding begins
Depart LGA on United UA 528
In-flight snack service (~2h 45m flight)
Land at Chicago O'Hare (ORD), Terminal 1
Collect luggage
Blue Line 'L' downtown (~40 min)
Arrive hotel, check in
Evening walk along the Chicago Riverwalk
Dinner: deep-dish pizza (Lou Malnati's or Giordano's)
Back to hotel
Day 2
Day 2 · The Loop & Millennium Park
$124
Breakfast at hotel
Walk to Millennium Park
Photos at Cloud Gate ('The Bean')
Stroll Lurie Garden & Pritzker Pavilion
Head to the Art Institute of Chicago
Explore galleries — American Gothic, Nighthawks, Impressionists
Lunch at the museum café
Walk down Michigan Avenue
Return to hotel, rest
Dinner in the West Loop (Randolph 'Restaurant Row')
Back to hotel
Day 3
Day 3 · Architecture & the River
$192
Breakfast
Walk to the river dock
Chicago Architecture River Cruise (~90 min)
Explore around the Wrigley Building & Tribune Tower
Lunch near the Magnificent Mile
Shopping along Michigan Avenue
360 Chicago observation deck (or Willis Skydeck)
Coffee break with a view
Dinner in River North
Optional rooftop bar, then back to hotel
Day 4
Day 4 · Museum Campus & Lakefront
$172
Breakfast
Rideshare to Museum Campus
Shedd Aquarium (arrive at opening)
Lunch with lakefront views
Field Museum (SUE the T. rex) or Adler Planetarium
Walk the lakefront trail toward the skyline viewpoint
Return to hotel, rest
Dinner: Chicago-style hot dogs or a classic steakhouse
Back to hotel
Day 5
Day 5 · Neighborhoods & Free Time
$138
Breakfast
'L' train to Wicker Park / Bucktown
Browse indie shops, murals & cafés
Lunch at a trendy neighborhood spot
Head to Lincoln Park — free zoo & conservatory
Walk along North Avenue Beach
Coffee & relax
Return to hotel
Farewell dinner (reserve in advance)
Back to hotel, begin packing
Day 6
Day 6 · Departure Day
$363
Breakfast & final packing
Check out, store bags if needed
Last stroll / souvenir shopping downtown
Lunch near the hotel
Rideshare / Blue Line to O'Hare (~40 min)
Arrive ORD Terminal 1, check in & drop bag
Security screening
Coffee at the gate
Boarding begins
Depart ORD on United UA 531
Arrive LaGuardia — welcome home!
Your turn
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