The Five On It • Chicago Guide

Five Chicago guide plans, already made.

Stop comparing options and building your own itinerary. We have already done it, every pick includes the full plan, insider tips, reservation advice, maps, backups, and the exact order to do it in.

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What's inside

Five guides, planned down to the minute

Every one runs start to finish, the spots, the timing, the order to do them in, plus reservations, maps, budgets, and a backup for each.

01
The Fun OneBold small plates, then cocktails in a hidden room.
02
The Romantic OneA dim, lush dining room, then a rooftop over the park.
03
The Glamorous OneA Parisian steakhouse, then live jazz around the corner.
04
The Italian OneCozy-glam Italian, then a drink with a view.
05
The Easy OneNo-reservations small plates, then a lakefront walk.
The first of five · a first taste
7:00 PM
Girl & the Goat

Stephanie Izard's Fulton Market flagship is loud, warm and built for sharing, bold, live-fire cooking (the famous goat dishes, the wood-oven pig face, roasted vegetables that convert skeptics) in a buzzing…

9:30 PM
Revealed inside

The West Loop is thick with excellent bars, walk a few blocks to one of the neighbourhood's cocktail dens for a nightcap. It's the best drinking district in the city, so you won't have to go far.

Revealed inside

The reservation is the hard part, it books up weeks ahead for weekends, and it's the anchor of the night. The bar area takes walk-ins if you miss the dining room.

+ 1 more
Revealed inside

Ten minutes of walking beats an expensive third drink, every time.

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A note from us

From us to you

We've done every one of these guides ourselves.

Some are where we celebrate birthdays. Some are where we take friends visiting Chicago. Some have just become our favorite “we don't even need to think about it” go-tos.

These are the guides we recommend to the people we care about most.

Now go enjoy it,

The Five On It
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