By Liam The first official day of Summer is Saturday and there’s still plenty of time to snag great Summer flight deals from Chicago. For readers from the New York area, we covered 20 of the best deals from NYC area airports last week.
While you may struggle to find great deals for the remainder of June, this is the perfect time to book an August or September vacation. There are even some superb deals left in July from O’Hare and Midway alike. Regardless, here’s a list of 25 of the best round trip Summer flight deals from Chicago, in no particular order.
Note that all prices are valid as of the time of writing. They’re subject to change quickly so it’s wise to book early. Also a lot of these deals involve basic economy fares, which are best for travelers who can pack light and stick to their original flight. More flexibility will cost you a bit more, but you may still find the price worth it.
Summer Flight Deals from Chicago
1. Las Vegas $98
While it might be blazing hot in Las Vegas during the Summer, you can still enjoy its legendary nightlife. Summer flight deals from O’Hare start at just $98 round trip on Spirit Airlines. Las Vegas is also within driving distance of National Parks like Zion and Bryce Canyon if you want to beat the heat.
2. Madrid $363
In late September, you can find round trip flights to Spain’s capital Madrid for just $363 on American from ORD. On the way back, there’s a stop but the price certainly can’t be beaten. You may even be able to catch a Real Madrid match at the Bernabeu or Atletico Madrid game at the Metropolitano. If not, you can still enjoy the tapas culture, Prado Museum and Plaza Mayor.
3. Savannah $83
Savannah recently made our list of 10 overlooked US cities. It’s one of the most beautiful cities in the US and you can fly there from Midway on Allegiant for just $83 round trip this Summer. Head to Forsyth Park then toward the historic district and admire all of the Spanish oak moss.
4. Pittsburgh $77
Pittsburgh also made our list of overlooked US cities and there’s plenty to do in the Steel City during Summer time. One of the best Summer flight deals on the list, you can snag round trip flights to Pittsburgh for $77 on Southwest from Midway Airport.
5. Washington DC $100
Head to our nation’s capital for just $100 round trip on Spirit from O’Hare. Washington DC has plenty of monuments, museums and eclectic food to enjoy this Summer. First time visitors should head to the National Mall to see the Washington Monument, Lincoln Memorial and Veterans’ Memorials. The National Museum of African American History and Culture is also right there and well worth the stop.
6. Cartagena $289
If you go to Cartagena, Colombia during the Summer (low season) you may be able to find good hotel deals. At the very least, the Summer flight deals are great, as round trips from Chicago start at $289 on Copa, with one stop. Cartagena is a vibrant and colorful city on Colombia’s Caribbean coast. The walled old town is beautiful and full of Spanish colonial architecture. The San Felipe de Barajas Fort is also a must visit.
7. Minneapolis $77
Instead of taking an eight hour train up to the Twin Cities, take a quick flight. This Summer, you can fly from Chicago to Minneapolis for just $77 round trip on Southwest from Midway or on United from O’Hare. There’s no doubt that Summer is the best time to visit the area and there are plenty of nearby lakes to cool off at.
8. Seattle $127
Summer is also the best season to head to Seattle. With $127 round trip Summer flight deals on Alaska Airlines, what are you waiting for? The Space Needle and Pike Place Market are two iconic symbols of this Pacific Northwest metropolis. Then, you can head on the ferry to an island like Bainbridge or Vashon.
9. Mexico City $266
I spent 2024 in Chicago but currently live in Mexico City and I’m obviously partial to it. The Summer is admittedly not the best time to go, with frequent afternoon rain, but there will be fewer crowds if you don’t mind it. There are enough things to do in Mexico City to fill a month, or longer. Check out our guide to Mexico City’s Centro Historico and the best day trips from CDMX before heading there. If you only have a little time, Chapultepec Park, the Teotihuacan Pyramids, Zocalo and Condesa/Roma neighborhoods are where you may want to check out. From ORD, Summer flights start at just $266 round trip on VivaAerobus.
10. Miami $128
Hit South Beach this Summer with $144 round trip flights to Miami on United. You can also get to nearby Fort Lauderdale for $128 on Spirit. Miami has cheap flights to plenty of beautiful Caribbean and South American destinations, so it could be a good stopping point on the way to somewhere else.
11. Houston $112
Houston’s another city with cheap flights to Central and South American destinations. On Spirit, from ORD, you can get to Houston for just $112 round trip. Of course, Houston also has great museums like the Menil Collection and the Museum of Fine Arts. Houston sometimes gets a bad rap for being so spread out but there’s no shortage of things to do. Rice University and Buffalo Bayou Park are worth a stop as well.
12. Cancun $220 Spirit
Sure, there are beaches in Chicago but if you want the resort experience, or want to explore the Yucatan peninsula, head to Cancun. Round trip flights start at just $220 on Spirit Airlines. Mexico just completed a tourist train project which connects Cancun to beautiful cities like Valladolid and Merida. Also, there are plenty of beach towns in the area like Playa del Carmen, Cozumel and Tulum.
13. Detroit $77
Although it’s not a city usually associated with tourism, Detroit is having a resurgence right now. The skyline is quite impressive and you can get a good view from Hart Plaza on the Detroit Riverwalk. Try the iconic Detroit style pizza at Buddy’s or Loui’s and catch a Tigers game at Comerica Park. Belle Isle Park, on an island in the Detroit River, is also beautiful and Detroit Institute of Arts, on the Wayne State campus, is an excellent museum. From Chicago, you can get to Detroit on Southwest from Midway or United from O’Hare for just $77 round trip.
14. New York $110
From Second City, head to the USA’s “First City” for just $110 from ORD to LaGuardia on Spirit. I’d highly recommend visiting NYC in September after Labor Day when the crowds thin out and the weather is still beautiful.
15. Boston $125
Boston is one of the most historic cities in the US and is a good Summer destination. You can fly from O’Hare to Boston and back on United for just $125. Boston Common, Fenway Park and Faneuil Hall Marketplace are some of the most iconic places in the city. You’ll also want to fly into Boston to visit Cape Cod.
16. Calgary $212
While you can’t get this price during the world famous Calgary Stampede in a few weeks, you can still head to Alberta this Summer for cheap. Round trip flights on United start at $212 and I saw a fare for under $200 on WestJet that could pop up again. Calgary is a gateway to the beautiful Canadian Rockies. Banff National Park is only 90 minutes away from Calgary and Jasper National Park is four hours away.
17. Nashville $77
Southwest has a bunch of great Summer flight deals from Midway and this is no exception. Head to Nashville for just $77 round trip and enjoy its vibrant nightlife and live music. Nashville is called the Music City for a reason and is a country music hub. It is also known for its hot chicken.
18. Myrtle Beach $106
Hit an east coast beach this Summer for just $106 round trip on Spirit Airlines from O’Hare. TripAdvisor recently ranked Myrtle Beach a top three Summer destination in the US for American citizens. That makes sense, given there are miles of sandy beaches in this South Carolina city. You could also tack on Charleston, which is two hours away, and make a road trip out of it.
19. Guadalajara $252
Guadalajara is one of Mexico’s biggest cities and the home of Mariachi. It’s also just an hour away from the famous town of Tequila, where the famous alcoholic drink originates from. Guadalajara itself has beautiful public plazas, churches and great food like tortas ahogadas and birria. While it is currently rainy season, $252 round trip on VivaAerobus from ORD is still a great deal.
20. Grand Rapids $77
Grand Rapids, Michigan is one of the best kept secrets in the US. It has been called “Beer City USA” as it has over 40 breweries. It is also home to the Gerald Ford Presidential Library and Frederik Meijer Gardens & Sculpture Park and just 30 minutes away from Lake Michigan beaches. From ORD on United and MDW on Southwest, round trip flights start at just $77.
21. Guatemala $200
Guatemala quickly became one of my favorite countries to travel in. Between the beautiful colonial city of Antigua, Lake Atitlan and the incredible Acatenango and Fuego volcanoes, there’s plenty to do during one week in Guatemala. This Summer, you can travel to Guatemala City and back for just $200 on United.
22. Fort Myers $100
Fort Myers is where you want to fly into for Florida’s iconic Gulf Coast beaches. So, at just $100 round trip on Spirit, this is one of the better Summer flight deals on the list. Sanibel Island and Captiva Island are two popular nearby vacation spots.
23. St. Louis $77
St. Louis is another place that was on our list of overlooked US cities to visit. It is home to the famous gateway arch and also has its own style of pizza and BBQ. Forest Park and the National Blues Museum are two essential stops other than the gateway arch. Round trip flights to Missouri’s second-largest city start at just $77 from MDW on Southwest.
24. Monterrey $213
Monterrey is the second-largest metropolitan area in Mexico behind Mexico City. The Northern Mexican city doesn’t receive a ton of tourism but there are plenty of things to do in and around Monterrey. Fundidora Park used to be the old Monterrey Foundry and is a great example of urban renewal. Then, check out Monterrey’s Barrio Antiguo and the Paseo de Santa Lucia along the river.
Monterrey also has a bunch of museums like the Museum of Contemporary Art, Palace Museum and Mexican Baseball Hall of Fame. There are also beautiful mountains and hikes in areas surrounding Monterrey like Chipinique Ecological Park, La Huasteca Ecological Park, Cerro de las Mitras and Cerra de la Silla. This Summer you can get roundtrip flights from O’Hare to Monterrey on VivaAerobus for $213.
25. Asheville $82
Speaking of mountains, Asheville is a gateway to Great Smoky Mountains National Park. With the last of our 25 Summer flight deals from Chicago, head to Asheville for $82 from Midway on Allegiant. Like Grand Rapids, Asheville has a lot of breweries per capita and also boasts a big farm-to-table food scene. Downtown is quaint and walkable, while the Biltmore Estate and North Carolina Arboretum are worth stops as well.