Eat well.
Sip smart.
Keep it local.

Browse recurring Monday food and drink specials in Chicago. The compact directory below keeps every schedule and source easy to scan.

CHEERS
TO THAT

MORE HAPPY
LESS SPENDY

Other weekdays

More Chicago restaurant deals

Browse all specials

Deals by day

Monday Restaurant Specials in Chicago — Page 3

Back to Chicago

Specials 49–50 of 50, from 49 local venues.

Whiskey Business Food & Drinks

$5 Miller Lites, $7 Jim Beam highballs and $8 Wagyu smash burgers

Monday–Friday · 4:00 PM–6:00 PM Wicker Park Verified Jul 26, 2026 Source

Wildfire Chicago Food & Drinks

$6 draught beers, $8 glasses of Wildfire chardonnay and cabernet sauvignon, $10 flatbreads

Monday–Friday · 5:00 PM–6:00 PM River North Verified Jul 27, 2026 Official source Website