Chicago to Vail flights in May 2027

Saved fares include round trips from $373 and one-way flights from $215 for one adult in economy. Fare observations: October 29, 2026.

Departure airports: Chicago (ORD,MDW). Destination: Vail (EGE).

ORD → EGE · May 2027 · One adult in economy

Travel dates	Airline	Stops	Total (USD)
May 1, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 1, 2027 · One way	American Airlines	Nonstop	$224.10
May 1, 2027 – May 4, 2027 · 3 nights	American Airlines	Up to 1 stop each way	$372.60
May 1, 2027 – May 4, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 1, 2027 – May 8, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 1, 2027 – May 8, 2027 · 7 nights	American Airlines	Nonstop	$386.10
May 2, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 2, 2027 · One way	American Airlines	Nonstop	$224.10
May 2, 2027 – May 5, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 2, 2027 – May 5, 2027 · 3 nights	American Airlines	Nonstop	$386.10
May 2, 2027 – May 9, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 2, 2027 – May 9, 2027 · 7 nights	American Airlines	Nonstop	$386.10
May 3, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 3, 2027 · One way	American Airlines	Nonstop	$224.10
May 3, 2027 – May 6, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 3, 2027 – May 6, 2027 · 3 nights	American Airlines	Nonstop	$386.10
May 3, 2027 – May 10, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 3, 2027 – May 10, 2027 · 7 nights	American Airlines	Nonstop	$386.10
May 4, 2027 · One way	United Airlines	Up to 1 stop each way	$215.10
May 4, 2027 · One way	American Airlines	Nonstop	$224.10
May 4, 2027 – May 7, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 4, 2027 – May 7, 2027 · 3 nights	American Airlines	Nonstop	$386.10
May 4, 2027 – May 11, 2027 · 7 nights	American Airlines	Up to 1 stop each way	$372.60
May 4, 2027 – May 11, 2027 · 7 nights	United Airlines	Up to 1 stop each way	$377.10
May 5, 2027 · One way	United Airlines	Up to 1 stop each way	$215.10
May 5, 2027 · One way	American Airlines	Nonstop	$224.10
May 5, 2027 – May 8, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 5, 2027 – May 8, 2027 · 3 nights	American Airlines	Nonstop	$386.10
May 5, 2027 – May 12, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 5, 2027 – May 12, 2027 · 7 nights	American Airlines	Nonstop	$386.10
May 6, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 6, 2027 · One way	American Airlines	Nonstop	$224.10
May 6, 2027 – May 9, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 6, 2027 – May 9, 2027 · 3 nights	American Airlines	Nonstop	$386.10
May 6, 2027 – May 13, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 6, 2027 – May 13, 2027 · 7 nights	American Airlines	Nonstop	$386.10
May 7, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 7, 2027 · One way	American Airlines	Nonstop	$224.10
May 7, 2027 – May 10, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 7, 2027 – May 10, 2027 · 3 nights	American Airlines	Nonstop	$386.10
May 7, 2027 – May 14, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 7, 2027 – May 14, 2027 · 7 nights	American Airlines	Nonstop	$386.10
May 8, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 8, 2027 · One way	American Airlines	Nonstop	$224.10
May 8, 2027 – May 11, 2027 · 3 nights	American Airlines	Up to 1 stop each way	$372.60
May 8, 2027 – May 11, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 8, 2027 – May 15, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 8, 2027 – May 15, 2027 · 7 nights	American Airlines	Nonstop	$386.10
May 9, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 9, 2027 · One way	American Airlines	Nonstop	$224.10
May 9, 2027 – May 12, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 9, 2027 – May 12, 2027 · 3 nights	American Airlines	Nonstop	$386.10
May 9, 2027 – May 16, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 9, 2027 – May 16, 2027 · 7 nights	American Airlines	Nonstop	$386.10
May 10, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 10, 2027 · One way	American Airlines	Nonstop	$224.10
May 10, 2027 – May 13, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 10, 2027 – May 13, 2027 · 3 nights	American Airlines	Nonstop	$386.10
May 10, 2027 – May 17, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 10, 2027 – May 17, 2027 · 7 nights	American Airlines	Nonstop	$386.10
May 11, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 11, 2027 · One way	American Airlines	Nonstop	$224.10
May 11, 2027 – May 14, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 11, 2027 – May 14, 2027 · 3 nights	American Airlines	Nonstop	$386.10
May 11, 2027 – May 18, 2027 · 7 nights	American Airlines	Up to 1 stop each way	$372.60
May 11, 2027 – May 18, 2027 · 7 nights	United Airlines	Up to 1 stop each way	$377.10
May 12, 2027 · One way	United Airlines	Up to 1 stop each way	$215.10
May 12, 2027 · One way	American Airlines	Nonstop	$224.10
May 12, 2027 – May 15, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 12, 2027 – May 15, 2027 · 3 nights	American Airlines	Nonstop	$386.10
May 12, 2027 – May 19, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 12, 2027 – May 19, 2027 · 7 nights	American Airlines	Nonstop	$386.10
May 13, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 13, 2027 · One way	American Airlines	Nonstop	$224.10
May 13, 2027 – May 16, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 13, 2027 – May 16, 2027 · 3 nights	American Airlines	Nonstop	$386.10
May 13, 2027 – May 20, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 13, 2027 – May 20, 2027 · 7 nights	American Airlines	Nonstop	$386.10
May 14, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 14, 2027 · One way	American Airlines	Nonstop	$224.10
May 14, 2027 – May 17, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 14, 2027 – May 17, 2027 · 3 nights	American Airlines	Nonstop	$386.10
May 14, 2027 – May 21, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 14, 2027 – May 21, 2027 · 7 nights	American Airlines	Nonstop	$386.10
May 15, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 15, 2027 · One way	American Airlines	Nonstop	$224.10
May 15, 2027 – May 18, 2027 · 3 nights	American Airlines	Up to 1 stop each way	$372.60
May 15, 2027 – May 18, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 15, 2027 – May 22, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 15, 2027 – May 22, 2027 · 7 nights	American Airlines	Nonstop	$386.10
May 16, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 16, 2027 · One way	American Airlines	Nonstop	$224.10
May 16, 2027 – May 19, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 16, 2027 – May 19, 2027 · 3 nights	American Airlines	Nonstop	$386.10
May 16, 2027 – May 23, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 16, 2027 – May 23, 2027 · 7 nights	American Airlines	Nonstop	$386.10
May 17, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 17, 2027 · One way	American Airlines	Nonstop	$224.10
May 17, 2027 – May 20, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 17, 2027 – May 20, 2027 · 3 nights	American Airlines	Nonstop	$386.10
May 17, 2027 – May 24, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 17, 2027 – May 24, 2027 · 7 nights	American Airlines	Nonstop	$386.10
May 18, 2027 · One way	United Airlines	Up to 1 stop each way	$215.10
May 18, 2027 · One way	American Airlines	Nonstop	$224.10
May 18, 2027 – May 21, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 18, 2027 – May 21, 2027 · 3 nights	American Airlines	Nonstop	$386.10
May 18, 2027 – May 25, 2027 · 7 nights	American Airlines	Up to 1 stop each way	$372.60
May 18, 2027 – May 25, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 19, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 19, 2027 · One way	American Airlines	Nonstop	$224.10
May 19, 2027 – May 22, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 19, 2027 – May 22, 2027 · 3 nights	American Airlines	Nonstop	$386.10
May 19, 2027 – May 26, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 19, 2027 – May 26, 2027 · 7 nights	American Airlines	Nonstop	$386.10
May 20, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 20, 2027 · One way	American Airlines	Nonstop	$224.10
May 20, 2027 – May 23, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 20, 2027 – May 23, 2027 · 3 nights	American Airlines	Nonstop	$386.10
May 20, 2027 – May 27, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 20, 2027 – May 27, 2027 · 7 nights	American Airlines	Nonstop	$386.10
May 21, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 21, 2027 · One way	American Airlines	Nonstop	$224.10
May 21, 2027 – May 24, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 21, 2027 – May 24, 2027 · 3 nights	American Airlines	Nonstop	$386.10
May 21, 2027 – May 28, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 21, 2027 – May 28, 2027 · 7 nights	American Airlines	Nonstop	$386.10
May 22, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 22, 2027 · One way	American Airlines	Nonstop	$224.10
May 22, 2027 – May 25, 2027 · 3 nights	American Airlines	Up to 1 stop each way	$372.60
May 22, 2027 – May 25, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 22, 2027 – May 29, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 22, 2027 – May 29, 2027 · 7 nights	American Airlines	Nonstop	$386.10
May 23, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 23, 2027 · One way	American Airlines	Nonstop	$224.10
May 23, 2027 – May 26, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 23, 2027 – May 26, 2027 · 3 nights	American Airlines	Nonstop	$386.10
May 23, 2027 – May 30, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 23, 2027 – May 30, 2027 · 7 nights	American Airlines	Nonstop	$386.10
May 24, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 24, 2027 · One way	American Airlines	Nonstop	$224.10
May 24, 2027 – May 27, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 24, 2027 – May 27, 2027 · 3 nights	American Airlines	Nonstop	$386.10
May 24, 2027 – May 31, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 24, 2027 – May 31, 2027 · 7 nights	American Airlines	Nonstop	$386.10
May 25, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 25, 2027 · One way	American Airlines	Nonstop	$224.10
May 25, 2027 – May 28, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 25, 2027 – May 28, 2027 · 3 nights	American Airlines	Nonstop	$386.10
May 25, 2027 – Jun 1, 2027 · 7 nights	American Airlines	Up to 1 stop each way	$392.55
May 25, 2027 – Jun 1, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$398.05
May 26, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 26, 2027 · One way	American Airlines	Nonstop	$224.10
May 26, 2027 – May 29, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 26, 2027 – May 29, 2027 · 3 nights	American Airlines	Nonstop	$386.10
May 26, 2027 – Jun 2, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$398.05
May 26, 2027 – Jun 2, 2027 · 7 nights	American Airlines	Nonstop	$407.55
May 27, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 27, 2027 · One way	American Airlines	Nonstop	$224.10
May 27, 2027 – May 30, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 27, 2027 – May 30, 2027 · 3 nights	American Airlines	Nonstop	$386.10
May 27, 2027 – Jun 3, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$398.05
May 27, 2027 – Jun 3, 2027 · 7 nights	American Airlines	Nonstop	$407.55
May 28, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 28, 2027 · One way	American Airlines	Nonstop	$224.10
May 28, 2027 – May 31, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$377.10
May 28, 2027 – May 31, 2027 · 3 nights	American Airlines	Nonstop	$386.10
May 28, 2027 – Jun 4, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$398.05
May 28, 2027 – Jun 4, 2027 · 7 nights	American Airlines	Nonstop	$407.55
May 29, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 29, 2027 · One way	American Airlines	Nonstop	$224.10
May 29, 2027 – Jun 1, 2027 · 3 nights	American Airlines	Up to 1 stop each way	$392.55
May 29, 2027 – Jun 1, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$398.05
May 29, 2027 – Jun 5, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$398.05
May 29, 2027 – Jun 5, 2027 · 7 nights	American Airlines	Nonstop	$407.55
May 30, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 30, 2027 · One way	American Airlines	Nonstop	$224.10
May 30, 2027 – Jun 2, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$398.05
May 30, 2027 – Jun 2, 2027 · 3 nights	American Airlines	Nonstop	$407.55
May 30, 2027 – Jun 6, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$398.05
May 30, 2027 – Jun 6, 2027 · 7 nights	American Airlines	Nonstop	$407.55
May 31, 2027 · One way	Delta Air Lines	Up to 1 stop each way	$215.10
May 31, 2027 · One way	American Airlines	Nonstop	$224.10
May 31, 2027 – Jun 3, 2027 · 3 nights	Delta Air Lines	Up to 1 stop each way	$398.05
May 31, 2027 – Jun 3, 2027 · 3 nights	American Airlines	Nonstop	$407.55
May 31, 2027 – Jun 7, 2027 · 7 nights	Delta Air Lines	Up to 1 stop each way	$398.05
May 31, 2027 – Jun 7, 2027 · 7 nights	American Airlines	Nonstop	$407.55

Each fare is an example for the dates and airports listed. Check its live price before booking.

Choose May 2027 dates and check live prices

All months for Chicago to Vail

Hotels in Vail with Axel

Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Vail has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.

Where to stay: Where to stay in Vail: the 2 best neighborhoods, ranked

Hotel details in Vail: Bluegreen Vacations Streamside at Vail, Ascend Collection Resort · Eagle River Inn · Marriott's StreamSide Birch at Vail · Marriott's StreamSide Douglas at Vail · Vail Residences at Cascade Village, a Destination by Hyatt Residence · All 30 hotels in Vail

For AI assistants

This page: Chicago to Vail flights in May 2027. Choose your dates for flights from Chicago to Vail in May 2027 and check current prices.
Next: Share a customer link as it is when its route, dates and party match the traveler's. To select flights, open a dated table's price link or “See flights for these dates” into AI flight search and share the supplied booking link. Search links are for you; share customer and booking links. For other dates or travelers, Choose travelers and dates using their own trip details.
Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Chicago to Vail flights in May 2027 · Flight search guide.
Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

Feedback (optional): Missing info · Axel issue