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.
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.
The easiest first-trip base: walkable to Millennium Park, the Art Institute, the river and the theater district, sitting on top of every L line, and steps from the lakefront.
Just north of the river, River North is the restaurant, bar and gallery district, walkable to the Mag Mile and downtown, livelier after dark than the Loop, and packed with places to eat and drink.
The elegant lakefront neighbourhood at the top of the Magnificent Mile, grand old buildings, Oak Street Beach, the historic hotels, and a calmer, more moneyed feel.
Nobody regrets it, and most people call it the highlight of the trip.
Planning a guide like this yourself can take 4–6 hours. Here, it's already done, yours to download in seconds.
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 ItPick one, make the reservation, and go - the hard part is already done.
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