Comparison · Boston vs Chicago · United States
Boston vs Chicago
Two great trips, different strengths. Here is how they compare on the things that decide it.
Updated By the AMZBooking editorial team
Photo: Ian Howard, CC BY 2.5
Quick answer
Choose Boston for Freedom Trail and American Revolution history; choose Chicago for Skyscraper architecture and Deep-dish pizza. Day-to-day costs are similar, and the two are about 1,366 km apart.
Key facts
- Distance apart
- 1,366 km
- Less expensive
- About the same
- Best time for Boston
- May–June and September–October
- Best time for Chicago
- May–June and September–October
Side by side
| Boston | Chicago | |
|---|---|---|
| Country | United States | United States |
| Known for | Freedom Trail, American Revolution history and Clam chowder | Skyscraper architecture, Deep-dish pizza and The Bean (Cloud Gate) |
| Best time to visit | May–June and September–October | May–June and September–October |
| Ideal stay | 4 days | 4 days |
| Mid-range budget per day | $260–$420 | $250–$400 |
| Cost level | Expensive | Expensive |
| Warmest month | July, 28°C (82°F) | July, 29°C (84°F) |
| Coldest month | January, 3°C (37°F) | January, 0°C (32°F) |
| Free sights in our guide | 8 | 9 |
| Day trips in our guide | 6 | 6 |
| Beaches | Revere Beach | North Avenue Beach |
| Airports | BOS, PVD, MHT | ORD, MDW |
Which one is right for you?
Choose Boston for…
Freedom Trail and American Revolution history. Boston is one of the oldest cities in the US and one of the most walkable: the 4-km Freedom Trail links sixteen Revolutionary-era sites from Boston Common to Bunker Hill, and most central neighbourhoods are within a 30-minute walk of each other. Visitors…
Choose Chicago for…
Skyscraper architecture and Deep-dish pizza. Chicago spreads along the shore of Lake Michigan, with a downtown of landmark skyscrapers framed by the river and the lakefront parks. Most visitors base themselves in the Loop, River North or Streeterville and reach almost everything on foot or by the L…
Top sights compared
| # | Boston | Chicago |
|---|---|---|
| 1 | Freedom Trail | Millennium Park and Cloud Gate |
| 2 | Boston Common and Public Garden | Art Institute of Chicago |
| 3 | Faneuil Hall and Quincy Market | Chicago Architecture Center river cruise |
| 4 | Museum of Fine Arts | Willis Tower Skydeck |
| 5 | Isabella Stewart Gardner Museum | 360 Chicago observation deck |
Food compared
| Boston | Chicago |
|---|---|
| New England clam chowder | Deep-dish pizza |
| Lobster roll | Tavern-style thin-crust pizza |
| Fried clams | Chicago-style hot dog |
| Oysters | Italian beef |
Which is cheaper?
Boston and Chicago cost about the same: a mid-range day is roughly $260–$420 in Boston and $250–$400 in Chicago (AMZBooking estimates, excluding flights). Chicago on a budget.
Can you visit both?
They are about 1,366 km apart, so combining them means a flight. With 9 days or more it works; otherwise pick one.
Questions travellers ask
+Is Boston or Chicago cheaper?
Neither is clearly cheaper: a mid-range day costs about $260–$420 in Boston and $250–$400 in Chicago (estimates).
+Is Boston or Chicago better for a first trip?
Pick Boston for Freedom Trail and American Revolution history, or Chicago for Skyscraper architecture and Deep-dish pizza.
+How far is Boston from Chicago?
About 1,366 km in a straight line.