Arriv guide · Chicago
Chicago weekend
Chicago, IL · 3-day weekend getaway · 9 places
By ArrivLast checked
Deep dish, architecture cruises, and rooftop season. 3 days is enough for two neighborhoods and one long meal, once you accept that the third neighborhood was never going to happen. This Chicago plan picks the two and leaves an hour in the afternoon to sit down. Arrive Friday afternoon if you can make the flights work, because a full Saturday is the whole payoff. The first evening then goes to dinner and a walk, which is a better start than a supermarket run. This guide maps 9 hand-picked places across deep dish & classics, architecture & sights, and rooftops & bars in Chicago, IL, grouped the way you would use them once you are on the ground. Treat the order as a starting point, since your flights and your hotel will bend it anyway. Duplicate the trip in Arriv, drag the stops that do not suit you, add the hotel, and send the link to whoever else is coming.
Stays on this map
Hotels and rentals near these pins.
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How to use this Chicago guide
- Follow the day-by-day order as a starting spine, because it already accounts for what sits near what. 3 days is the intended pace, and once you duplicate the trip you can stretch it or compress it to fit the flights.
- Day 1 assumes you are checked in and moving, so the first big block starts on a morning that is already yours. Land the night before if the schedule allows it.
- 6 stops carry a note about reservations, timing, or where to eat after the main event. Read those first, because they are the ones that change what you end up booking.
- The lists are themed on purpose, which is why they hold together as sets: Deep dish & classics, Architecture & sights, Rooftops & bars. Use them when you have finished the scheduled stops and still have an evening to fill.
- Pin the map so you have it on your phone at the airport. Duplicate into Arriv when you are ready to lock dates, add hotels, and share the plan with everyone coming to Chicago.
3-day Chicago itinerary
Tap a stop to see it on the map. Adjust freely once it’s your trip.
Day 1Arrive + dinner + speakeasy
Girl & the Goat
4.7
809 W Randolph St, Chicago, IL 60607, USA
Tip — Big first-night dinner
The Violet Hour
4.6
1520 N Damen Ave, Chicago, IL 60622, USA
Tip — Speakeasy nightcap
Day 2Architecture cruise + deep dish + jazz
Chicago Architecture River Cruise
4.8
112 E Wacker Dr, Chicago, IL 60601, USA
Tip — The best intro to the city
Lou Malnati's Pizzeria
4.4
439 N Wells St, Chicago, IL 60654, USA
Tip — Deep dish — order when seated
Millennium Park
201 E Randolph St, Chicago, IL 60602, USA
Tip — The Bean photo op
Cindy's
4.4
12 S Michigan Ave, Chicago, IL 60603, USA
Tip — Golden-hour rooftop drinks
Green Mill Cocktail Lounge
4.3
4802 N Broadway, Chicago, IL 60640, USA
Tip — Late-set jazz
Day 3Italian beef + Navy Pier
Portillo's
4.4
100 W Ontario St, Chicago, IL 60610, USA
Tip — Italian beef before the airport
Navy Pier
4.6
600 E Grand Ave, Chicago, IL 60611, USA
Where to go in Chicago
9 places across 3 themed lists — use these when you want options beyond the day plan.
Deep dish & classics
439 N Wells St, Chicago, IL 60654, USA
100 W Ontario St, Chicago, IL 60610, USA
Chicago dogs and Italian beef, which is the two-item education you need before you go home.
809 W Randolph St, Chicago, IL 60607, USA
Stephanie Izard's flagship, so book well ahead, because the tables go weeks out.
Architecture & sights
112 E Wacker Dr, Chicago, IL 60601, USA
201 E Randolph St, Chicago, IL 60602, USA
The Bean and Crown Fountain, which sit close enough together that you can do both before lunch.
600 E Grand Ave, Chicago, IL 60611, USA
Rooftops & bars
12 S Michigan Ave, Chicago, IL 60603, USA
A rooftop inside the Chicago Athletic Association, which looks out over the park and fills up at golden hour.
1520 N Damen Ave, Chicago, IL 60622, USA
Speakeasy cocktails in Wicker Park, which sits far enough from the Loop that you should plan the ride.
4802 N Broadway, Chicago, IL 60640, USA
A jazz club since 1907, and one of Al Capone's old haunts, which the room will not let you forget.
Make this Chicago trip yours
Use this guide to duplicate the itinerary into your trips. Set dates, swap stops, invite your crew — then continue planning on the web or take it on the go in the Arriv app.