2 days in Chicago
Architecture, deep-dish and a lakefront skyline. Here's how to spend 2 days in Chicago: a realistic day-by-day plan you can copy and tweak. The best time for this 2 days Chicago trip is June, July and August. Budget roughly $150/person/day before flights.
Your 2 days Chicago itinerary, day by day
Day 1
Day 2
A starting point, not a script. Reshuffle it in the planner →
What 2 days in Chicago costs
What this trip costs
Estimates for planning, so check live prices before you book.
Have more or less time in Chicago?
2 days in Chicago: FAQ
Is 2 days enough for Chicago?+
2 days is enough to cover the main highlights of Chicago without rushing the essentials. The plan above balances the must-sees with time to wander.
What should I do on day 1 in Chicago?+
Start with Local food tour of Chicago, Central market & street-food lunch and Central market & street-food lunch. The full first day is mapped out above.
How much does 2 days in Chicago cost?+
Budget around $150 per person per day for a mid-range trip (stay, food and activities), before flights, so roughly $300 per person for 2 days. The cost breakdown above splits it by category.
When is the best time to visit Chicago?+
The best months to visit Chicago are June, July, August and September, when the weather suits sightseeing best.