Des Moines vs Chicago: Which City is Better to Visit in 2026?
City comparison: Des Moines vs ChicagoUpdated
- Overall pickChicago
The verdict
Chicago wins overall (8.8 vs 6.6 out of 10), taking 5 of 5 categories.
While Des Moines offers a charming Midwestern experience with its own unique attractions, Chicago's world-class cultural institutions, diverse culinary scene, and extensive transportation options make it the overall winner for most visitors. However, Des Moines may be preferable for those seeking a more relaxed, budget-friendly experience with a focus on local culture and outdoor activities.
Des Moines is significantly cheaper across housing, food, transport, and activities—allowing the same standard of living with roughly 40 % lower cost than Chicago. Chicago offers slightly milder and clearer summers, while both cities endure cold, snowy winters; overall Chicago’s longer clear-sky summer window gives it a slight edge.
Best for well-rounded travelers — Chicago edges ahead overall.
Choose Chicago if…
You care most about
- Cultural Attractions
- Cuisine
- Transportation
- Accommodation
- Nightlife
Overall scores are editorial ratings out of 10; category winners come from the per-category scores below. The overall pick is the higher overall score.
Overall scores
Des Moines
Chicago Winner
Category by category
| Category | Des Moines | Chicago | Edge |
|---|---|---|---|
| Cultural AttractionsComparison of museums, historical sites, and cultural experiences | 7 | 9 | Chicago |
| CuisineAnalysis of food scenes, local specialties, and dining experiences | 7 | 9 | Chicago |
| TransportationEvaluation of public transit systems, walkability, and ease of getting around | 6 | 9 | Chicago |
| AccommodationOverview of hotel options, neighborhoods, and accommodation costs | 7 | 8 | Chicago |
| NightlifeComparison of evening entertainment, bars, and nightlife scenes | 6 | 9 | Chicago |
Cultural Attractions: the details
Des Moines
- Des Moines Art Center – free admission and notable modern art collection
- State Historical Museum of Iowa – showcasing Iowa's rich history
- Salisbury House – historic mansion with art and rare book collections
Chicago
- The Art Institute of Chicago – one of the world's premier fine arts museums
- Field Museum – renowned natural history museum
- Museum of Science and Industry – largest science center in the Western Hemisphere
Cuisine: the details
Des Moines
- Farm-to-table restaurants showcasing local Iowa produce
- Iconic Steak de Burgo – Des Moines specialty
- Expanding craft beer scene with local breweries
Chicago
- Iconic deep-dish pizza and Chicago-style hot dogs
- Diverse ethnic neighborhoods offering authentic cuisines
- Michelin-starred restaurants and innovative dining experiences
Transportation: the details
Des Moines
- DART bus system covering major areas
- Bike-friendly with expanding trail network
- Easy to navigate by car with minimal traffic compared to larger cities
Chicago
- Extensive 'L' train system covering city and some suburbs
- Comprehensive bus network
- Divvy bike-sharing program and dedicated bike lanes
Accommodation: the details
Des Moines
- Affordable hotel options in downtown and suburban areas
- Unique bed and breakfasts in historic neighborhoods
- Limited luxury options compared to larger cities
Chicago
- Wide range of options from budget to ultra-luxury
- Historic hotels like The Drake and Palmer House
- Neighborhood rentals offering local experiences
Nightlife: the details
Des Moines
- East Village area with trendy bars and restaurants
- Live music venues like Wooly's and Hoyt Sherman Place
- Growing craft cocktail scene
Chicago
- Vibrant comedy scene including Second City
- World-class jazz and blues clubs
- Diverse nightlife districts like River North and Wrigleyville
Who should pick which
- Cost
- Des Moines
- Weather
- Chicago
- Culture
- Chicago
- Nightlife
- Chicago
- Families
- Chicago
Des Moines vs Chicago: Which Should You Visit?
Both Des Moines and Chicago are popular travel destinations, but they offer very different experiences. Whether you’re planning a quick getaway or a longer trip, understanding how they compare on weather, cost, things to do, and cultural depth helps you pick the right one for your travel style and budget.
Weather and Best Time to Visit
Chicago offers slightly milder and clearer summers, while both cities endure cold, snowy winters; overall Chicago’s longer clear-sky summer window gives it a slight edge.
Des Moines: Best months are June, July, August. 16 °F to 86 °F.
Chicago: Best months are mid-June, July, August. 22 °F to 83 °F.
Des Moines: Best months are June, July, August. 16 °F to 86 °F.
Chicago: Best months are mid-June, July, August. 22 °F to 83 °F.
Weather winner: chicago
Cost of Travel and Daily Budget
Des Moines is significantly cheaper across housing, food, transport, and activities—allowing the same standard of living with roughly 40 % lower cost than Chicago.
notably higher housing/rent costs
notably higher housing/rent costs
around 40 % lower overall cost in Des Moines
Sources: {‘name’: ‘Numbeo cost of living comparison’, ‘url’: ‘https://www.numbeo.com/cost-of-living/compare_cities.jsp?city1=Des+Moines%2C+IA&city2=Chicago%2C+IL&country1=United+States&country2=United+States’}, {‘name’: ‘BestPlaces cost of living comparison 2025’, ‘url’: ‘https://www.bestplaces.net/compare-cities/des_moines_ia/chicago_il/costofliving’}
Budget winner: des moines
Things to Do and Activities
Chicago’s roster of recurring summer festivals and large-scale events slightly outweighs Des Moines’ regional festivals for variety and prominence.
Activities winner: chicago
Culture, Heritage, and Local Life
Chicago’s cultural depth spans global culinary, historic neighborhoods, and institutional scale; Des Moines shines in regional arts and agriculture celebration.
Culture winner: chicago
The Bottom Line: Des Moines or Chicago?
Chicago takes the edge in 3 out of 4 categories. However, both destinations have distinct strengths, and the best choice depends on your priorities.
Consider visiting Des Moines if you prioritize lower costs. Choose Chicago if outdoor activities matters more to you.
Travel tips
- Consider visiting Des Moines during the Iowa State Fair in August for a quintessential Midwest experience.
- In Chicago, purchase a CityPASS for savings on major attractions.
- Des Moines is very driveable, but consider renting a bike to explore the extensive trail system.
- Book accommodations in Chicago well in advance, especially during summer and major events.
Frequently asked questions
Which city is more budget-friendly, Des Moines or Chicago?
Des Moines is generally more budget-friendly than Chicago. Accommodation, dining, and entertainment costs are typically lower in Des Moines, making it a more economical choice for budget-conscious travelers.
When is the best time to visit Des Moines?
The best time to visit Des Moines is from June to September when the weather is warm and outdoor events are plentiful. August is particularly popular due to the Iowa State Fair. Spring and fall offer mild temperatures and beautiful scenery, while winters can be cold with occasional snowfall.
When is the best time to visit Chicago?
The best time to visit Chicago is from April to May or September to October when temperatures are mild and tourist crowds are smaller. Summer (June to August) is peak tourist season with numerous festivals and events, but it can be crowded and humid. Winter can be harsh but offers unique experiences like the Christkindlmarket.
Is it possible to do a day trip from Des Moines to Chicago?
While it's technically possible, a day trip from Des Moines to Chicago is not recommended due to the distance (about 330 miles or 5-6 hours drive each way). Flying would be quicker but still limit your time in Chicago. It's better to plan at least an overnight stay to properly experience Chicago.
The two side by side
Des Moines
United States
A vibrant Midwestern city known for its political significance, thriving art scene, and quality of life
- Iowa State Capitol
- Des Moines Art Center
- Pappajohn Sculpture Park
- Iowa State Fair
- January: 20
- February: 25
- March: 40
- April: 60
- May: 75
- June: 95
- July: 100
- August: 98
- September: 80
- October: 65
- November: 35
- December: 30
Chicago
United States
A world-class city renowned for its architecture, cultural institutions, and diverse neighborhoods
- Willis Tower
- Millennium Park
- The Art Institute of Chicago
- Deep-dish pizza
- January: 30
- February: 35
- March: 50
- April: 65
- May: 80
- June: 90
- July: 100
- August: 95
- September: 85
- October: 75
- November: 55
- December: 70
